Month: September 2021

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 67622-86-0, name is 2-Methyl-1-(methylamino)propan-2-ol. A new synthetic method of this compound is introduced below., Safety of 2-Methyl-1-(methylamino)propan-2-ol

General procedure: The solution of boronic acid 4 (9.4 mg, 0.025 mmol, 5 mol%) and aminoalcohol (5.2 mg, 0.025 mmol, 5 mol%) was refluxed in toluene for12 h to remove water azeotropically. The mixture was allowed to coolto r.t. and toluene was removed in vacuo. Next, 1 M SnCl4 in CH2Cl2(25 muL, 0.025 mmol, 5 mol%) was added to a solution of the oxazaborolidine,methacrolein (43 muL, 0.5 mmol, 1 equiv), and cyclopentadiene(125 muL, 1.5 mmol, 3 equiv) in CH2Cl2 (2.5 mL) and the mixturewas stirred for 2 h at -78 C. The reaction was quenched with sat. aqNaHCO3 and extracted with Et2O. The combined organic phase waswashed with brine, and dried (Na2SO4). After filtration and removal ofsolvent, the crude product was purified by column chromatography(silica gel, pentane/Et2O 9:1) to afford the Diels-Alder adduct (67 mg,98%) as a colorless oil. The enantioselectivity was determined to be84% ee by GC analysis after conversion into the chiral acetal by(2R,4R)-pentane-2,4-diol.GC [ULBON HR-20M (PEG-20M), 100 C]: tR = 24.3 (minor), 26.0 min(major).1H NMR (400 MHz, CDCl3): delta = 9.70 (s, 1 H), 6.31 (dd, J = 2.9, 6.1 Hz, 1H), 6.11 (dd, J = 6.1, 3.0 Hz, 1 H), 2.87 (br s, 1 H), 2.81 (br s, 1 H), 2.22(dd, J = 3.8, 12.0 Hz, 1 H), 1.35-1.42 (m, 1 H), 1.22-1.28 (m, 1 H), 1.00(s, 3 H).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 67622-86-0, 2-Methyl-1-(methylamino)propan-2-ol.

Reference:
Article; Shimoda, Yasushi; Yamamoto, Hisashi; Synthesis; vol. 49; 1; (2017); p. 175 – 180;,
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As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 1805-32-9, name is 3,4-Dichlorobenzyl alcohol, molecular formula is C7H6Cl2O, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. Safety of 3,4-Dichlorobenzyl alcohol

General procedure: To a stirring mixture of the substrate (1 mmol) and MMTHClO4(7 mg) in CH3CN (3 mL), HMDS (0.75 mmol)was added at room temperature. After completion of thereaction, indicated by TLC, ethyl acetate: n-hexane (3:7),the mixture was filtered to separate the catalyst. The filtratewas washed with acetonitrile (5 mL). Removal of the solvent under reduced pressure gave almost pure productin good to high yields. Further purification was carriedout by column chromatography on silica gel (eluting withEtOAc:hexane = 1:4), if necessary.

With the rapid development of chemical substances, we look forward to future research findings about 1805-32-9.

Reference:
Article; Mashhadinezhad, Maryam; Shirini, Farhad; Mamaghani, Manouchehr; Journal of Nanoscience and Nanotechnology; vol. 19; 4; (2019); p. 2099 – 2107;,
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Adding a certain compound to certain chemical reactions, such as: 4415-73-0, 1,1-Cyclobutanedimethanol, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, 4415-73-0, blongs to alcohols-buliding-blocks compound. COA of Formula: C6H12O2

To a solution of cyclobutane-l,l-diyldimethanol (10.00 g, 86.1 mmol) in N,N- dimethylformamide (200 mL), imidazole (8.8 g, 129.1 mmol) and tert-butyldimethylsilyl chloride (12.98 g, 86.1 mmol) were added in one portion at 0 C. The reaction mixture was stirred at 0 C for 10 minutes and then warmed to room temperature for 4 hours. The reaction mixture was quenched with water (500 mL) and extracted with ethyl acetate (250 mL x 3). The combined organic layer was washed with water, brine, dried over MgS04 and concentrated. The resultant residue was purified by flash chromatography (120 g silica gel, 0- 20 % ethyl acetate in hexanes) to get the title compound as a colorless oil. NMR (300 MHz, CDCb): delta 3.71 (s, 1H), 3.69 (d, J= 5.0 Hz, 1H), 2.87 (t, J= 5.4 Hz, 1H), 2.00-1.72 (m, 6H), 0.91 (s, 6H), 0.10 (s, 6H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4415-73-0, its application will become more common.

Reference:
Patent; FGH BIOTECH, INC.; UESUGI, Motonari; KINCAID, John; HUFF, Joel; (150 pag.)WO2018/49080; (2018); A1;,
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Application of 22419-35-8, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.22419-35-8, name is 4,4-Difluorocyclohexanol, molecular formula is C6H10F2O, molecular weight is 136.1398, as common compound, the synthetic route is as follows.

To a solution of 4,4-difluorocyclohexanol (0.9 g) in toluene was added triphenyl phosphine (2.6 g) and di-t-butyldiazacarboxalate (1.82 g) and the reaction mixture stirred for 18 h. The reaction mixture was concentrated and methanol was added (13 mL). To the methanol solution HCl in dioxane (4M, 13 mL) was added. The reaction mixture was stirred for 3 h and concentrated. The reaction mixture was partitioned between water and ethyl acetate. The layers were separated and the aqueous layer was extracted 3* with ethyl acetate. The organic layer was dried with magnesium sulfate, filtered and concentrated. The title compound was used without purification in the preparation of 5-amino-1-(4,4-difluorocyclohexyl)-1H-pyrazole-4-carbonitrile. 400 MHz 1H NMR (CD3OD) delta 2.15-2.07 (m, 4H), 2.00-1.81 (m, 2H), 1.68-1.58 (m,2H). (M+H m/z=279.0).

The chemical industry reduces the impact on the environment during synthesis 22419-35-8, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Pfizer Inc; US2009/30003; (2009); A1;,
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Reference of 124-68-5, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.124-68-5, name is 2-Amino-2-methyl-1-propanol, molecular formula is C4H11NO, molecular weight is 89.1362, as common compound, the synthetic route is as follows.

D16(c) tert-butyl (l-hydroxy-2-methylpropan-2-yl)carbamate Di-tert-butyl dicarbonate (118 g, 539 mmol) was added slowly to a solution of 2-amino-2- methylpropan-lol (40 g, 449 mmol), sodium bicarbonate (0.82 g, 9.76 mmol) and sodium carbonate (0.82 g, 7.74 mmol) in l,4-dioxane(120 mL)/water (40 mL) at 0 C with stirring. Then, the reaction mixture was stirred at 25 C for 6 h, concentrated, and then EtOAc (1000 mL) was added. The organic phase was washed with water and saturated brine, dried over sodium sulphate, and concentrated in vacuo to afford the title compound (94 g, 111%>) as a white solid.

Statistics shows that 124-68-5 is playing an increasingly important role. we look forward to future research findings about 2-Amino-2-methyl-1-propanol.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; SANG, Yingxia; WAN, Zehong; ZHANG, Qing; WO2014/114694; (2014); A1;,
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Application of 4728-12-5, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 4728-12-5 as follows.

j0363] 2,2-Dimethyl-5-(hydroxymethyl)-1 ,3-dioxane (3a) (1.00 g) was dissolved in 22.8 mE of dichloromethane (MDC), and 700.0 mg of imidazole and 2.72 g of carbon tetrabromide were added thereto. After ice-cooling, 2.15 g of triphenylphosphine was thrther added, and the mixture was stirred at room temperature for 4 hours. Dichloromethane was distilled off under reduced pressure, and the resulting product was purified with silica gel chromatography (n-hexane:ethyl acetate=5: 1) to quantitatively obtain 1.60 g of 2,2-dimethyl-5-bromomethyl- 1 ,3-dioxane (Sb).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4728-12-5, its application will become more common.

Reference:
Patent; OTSUKA CHEMICAL CO., LTD.; YUASA, Hiroaki; OKAZAKI, Hiroki; (62 pag.)US2017/233421; (2017); A1;,
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Synthetic Route of 2566-44-1, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.2566-44-1, name is 2-Cyclopropylethanol, molecular formula is C5H10O, molecular weight is 86.13, as common compound, the synthetic route is as follows.

Synthesis of 3-((1R,5S,9r)-3-(2-cyclopropylethyl)-9-methoxy-3-azabicyclo[3.3.1]nonan-9-yl)benzamide hydrochloride To a solution of 2-cyclopropylethanol (0.21 g, 2.41 mmol) in dichloromethane (40 mL) was added silica (3 g), followed by pyridinium chlorochromate (0.52 g, 2.41 mmol). After 2 h of stirring the reaction mixture was filtered through a plug of silica and the desired aldehyde eluted with dichloromethane. The collected dichloromethane solution was concentrated to 30 mL and 3-((1R,5S,9r)-9-methoxy-3-azabicyclo[3.3.1]nonan-9-yl)benzamide hydrochloride (0.25 g, 0.80 mmol) added. To the resulting suspension was then added triethylamine (0.33 mL, 2.41 mmol) and sodium triacetoxyborohydride (0.51 g, 2.41 mmol) and the reaction mixture stirred for 3 hours. Concentrated aqueous ammonia was added and the mixture was extracted with dichloromethane (*3). The combined organic phases were concentrated and purified by reverse phase chromatography (C18) to give 3-((1R,5S,9r)-3-(2-cyclopropylethyl)-9-methoxy-3-azabicyclo[3.3.1]nonan-9-yl)benzamide (0.17 g, 62% yield). 2.0 M HCl in diethyl ether (0.25 mL, 0.50 mmol) was added to a solution of 3-((1R,5S,9r)-3-(2-cyclopropylethyl)-9-methoxy-3-azabicyclo[3.3.1]nonan-9-yl)benzamide (0.17 g, 0.50 mmol) in dichloromethane (5 mL) and then the volatiles removed. The residue was freeze-dried from water to give 3-((1R,5S,9r)-3-(2-cyclopropylethyl)-9-methoxy-3-azabicyclo[3.3.1]nonan-9-yl)benzamide hydrochloride (0.10 g, 55%)

Statistics shows that 2566-44-1 is playing an increasingly important role. we look forward to future research findings about 2-Cyclopropylethanol.

Reference:
Patent; Alkermes, Inc.; Wynn, Thomas Andrew; Alvarez, Juan C.; Moustakas, Demetri Theodore; Haeberlein, Markus; Pennington, Lewis D.; US2019/241524; (2019); A1;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 764-48-7, name is Ethylene Glycol Vinyl Ether. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C4H8O2

10109] Compound 4a, 1 -(6-hydroxynaphthalen-2-yl)etha-none, was synthesized by the inventors.10110] Specifically, starting materials for synthesis such as6-bromo-2-naphthol (2.0 g, 8.97 mmol), Pd(OAc)2 (100mg,0.45 mmol), DPPP (370 mg, 0.9 mmol), and ethylene glycol (3 mE) were added to an oven-dried flask with two necks and charged with argon gas. Oxygen present in the mixture was removed by adding the argon gas to the resulting mixture, and ethyleneglycolvinylether (2.41 mE, 27 mmol) and Et3N obtained distillation (3.12 mE, 22.4 mmol) were sequentially added. The mixture was stirred at 145 C. for 4 hours using a silicone oil containet The mixture was cooled to room temperature and stirred with dichloromethane (15 mE) and a 5% HC1 aqueous solution (30 mE) at room temperature for 1 hout The resulting mixture was extracted with dichioromethane (2×30 mE), and an organic layer was washed with water (30 mE) and dehydrated with anhydrous sodium sulfate (6 g). The solvent was removed under a reduced pressure condition of 40 mbar, and the resulting product was purified by column chromatography through a silica gel (Merck-silicagel 60, 230-400 mesh; using CH2C12 as a developer), thereby obtaining a solid, Compound 4a(1.33 g, 80%).10111] ?H NMR (CDC13, 300 MHz, 298 K, oe): 8.41 (1H, s), 7.98 (1H, dd, J=8.7, 1.6 Hz), 7.87 (1H, d, J=8.7 Hz), 7.70 (1H, d, J=8.7 Hz), 7.16 (1H, dd, J=8.7, 1.6 Hz), 5.4 (1H, s), 2.71 (3H, s); mp 172 C.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 764-48-7, Ethylene Glycol Vinyl Ether.

Reference:
Patent; POSTECH ACADEMY-INDUSTRY FOUNDATION; AHN, Kyo Han; MOON, Hyunsoo; KIM, Dokyoung; SINGHA, Subhankar; ROY, Basab; SAMBASIVAN, Sunderraman; (45 pag.)US2017/327509; (2017); A1;,
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Related Products of 52244-70-9, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 52244-70-9, name is 4-(4-Methoxyphenyl)-1-butanol. This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 7 [0194] (a) trans-4-[4-(4-Phenyl-cyclohexylamino)butyl]phenol [0195] (b) trans-4-{4-[Methyl(4-phenylcyclohexyl)amino]butyl}phenol [CHEMMOL-00019] [0196] Step 1: To an ice-cold, stirred solution of alcohol 16 (1.5 g, 8.3 mmol) in TBF (40 mL), under an N2 atmosphere, was added Et3N (1.7 mL, 12 mmol) followed by methanesulfonyl chloride (0.77 mL, 10 mmol). After 1 hour, the reaction mixture was partitioned between EtOAc and 1N HCl. The organic layer was washed with H2O, saturated NaHCO3, saturated NaCl, dried (Na2SO4), and filtered. Concentration under reduced pressure gave mesylate 17 (2.2 g, 100percent), which was used without further purification: 1H NMR (300 MHz, CD3OD) ? 7.10 (d, J=8.5 Hz, 2H), 6.82 (d, J=8.5 Hz, 2H), 4.25-4.20 (m, 2H), 3.75 (s, 31), 3.03 (s, 31), 2.62-2.56 (m, 2H), 1.73-1.40 (m, 4H).

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 52244-70-9, 4-(4-Methoxyphenyl)-1-butanol.

Reference:
Patent; Deorazio, Russell Joseph; Nikam, Sham Shridhar; Scott, Ian Leslie; Sherer, Brian Alan; Wise, Lawrence David; US2003/225164; (2003); A1;,
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With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.100058-61-5, name is 3-(Benzyloxy)cyclobutanol, molecular formula is C11H14O2, molecular weight is 178.23, as common compound, the synthetic route is as follows.Safety of 3-(Benzyloxy)cyclobutanol

Example lbb – Preparation of R Synthesis of 2-bromo-l-(bromomethyl)-l-(phenylmethoxy)ethane [0299] The mixture of 1 (60.1 g, 0.47 mol), benzyl bromide (80 g, 0.47 mol) and Hg2Cl2 (100 mg, 0.2 mmol) was heated to 150 C over night. TLC showed the reaction was completed. The product 2 (98 g, 70% yield) was obtained by distillation (180 C) in vacuum as a colorless oil. [0300] 1H NMR (400 MHz, CDCl3):7.37-7.28 (m, 5H), 4.65 (s, 2H), 3.82-3.77 (m, 1H), 3.56 (d, 4H, J=5.2 Hz). Synthesis of l-(methylsulfinyl)-l-methylthio-3-(phenylmethoxy)cyclobutane [0301] To the mixture of 3 (45.1 g, 0.36 mol) in THF (400 mL) was added n- BuLi (145 mL, 0.36 mol, 2.5 M) at -10 C under N2 drop wise. It was stirred further 2 h at this temperature. And then it was cooled to -78 C and the mixture of 2 (46.2 g, 0.15 mol) in THF (100 mL) was added drop wise over 0.5 h. The result mixture was stirred further 2 h at – 78 C and over night at r.t. It was quenched by the addition of H20 (100 mL) and the mixture was extracted with EtOAc (300 mL*3). The combined extracts were dried over Na2SC>4 and concentrated in vacuo to give the crude product. It was purified by column chromatography (Eluan: EtO Ac/Pet. ether= 1/2, v/v) to give the product 4 (30 g, 73% yield) as a yellow oil. [0302] 1H NMR (400 MHz, CDCl3):7.36-7.26 (m, 5H), 4.47 (d, 2H), 4.38-4.31 (m, 0.6H), 4.21-4.18 (m, 0.4H), 3.10-2.98 (m, 0.8H), 2.78-2.64 (m, 1.2 H), 2.55 (s, 1.2 H), 2.44 (s, 1.8 H), 2.42-2.15 (m, 2H), 2.12 (d, 3H). Synthesis of 3-(phenylmethoxy)cyclobutan-l-one [0303] To a solution of compound 4 (30 g, 0.1 1 mol) in dry ether (500 mL) was HC104 (22.5 mL, 35%) at 0 C drop wise, while keep the temperature bellow 10 C . It was stirred further 2 h at 0 C and over night at r.t. Solid NaHC03 and MgSC>4 were added and the resulting mixture was stirred further 0.5 h at r.t. It was filtered and the cake was washed with ether. The filtrate was concentrate in vacuo to give the crude product. It was purified by column chromatography (Eluant: EtOAc/Pet.ether=l/4, v/v) to give the product 5 (14.0 g, 72% yield) as a yellow oil. [0304] 1H NMR (400 MHz, CDC13): 7.39-7.25 (m, 5H), 4.52 (s, 2H), 4.40-4.34 (m, 1H), 3.26-3.10 (m, 4H). Synthesis of 3-(phenylmethoxy)cyclobutan-l-ol [0305] To the mixture of 5 (14.0 g, 79.46 mmol) in EtOH (150 mL) was added aBH4 (3.32 g, 87.40 mmol) at 0 C over 0.5 h. The resulting mixture was stirred further 2 h at 0 C and TLC showed the reaction was completed. The solvent was removed in vacuo and the residue was diluted with MeOH (100 mL) and quenched by HC1 (1M). The organic solvent was removed in vacuo and the residue was extracted with EtOAc (200 mL*3). The combined extracts were dried over Na2SC>4 and concentrated in vacuo to give the crude product. It was purified by column chromatography (Eluant: EtOAc/Pet.ether=l/4, v/v) to give the product 6 (14 g, 99% yield) as a yellow oil. [0306] 1H NMR (400 MHz, CDC13): 7.39-7.27 (m, 5H), 4.43 (s, 2H) 1H), 3.68-3.59 (m, 1H), 2.76-2.67 (m, 2H), 2.37 (br, 1H), 2.05-1.89 (m, 2H). Synthesis of 5-(phenylmethoxy)-2-[3-(phenylmethoxy)cyclobutoxy]pyrimidine [0307] To the mixture of 6 (10.5 g, 58.93 mmol) in DMSO (100 mL) was added NaH (3.06 g, 60%, 76.61 mmol) at r.t. The resulting mixture was stirred for 0.5 h at r.t, and then the mixture of 7 (13.0 g, 58.93 mmol) in DMSO (50 mL) was added drop wise over 10 min. The whole mixture was stirred further 0.5 h, TLC showed the reaction was completed. It was quenched by the addition of H20 (200 mL) and the mixture was extracted with EtOAc (200 mL*3). The combined extracts were dried over a2S04 and concentrated in vacuo to give the crude product. It was purified by column chromatography (Eluant: EtOAc/Pet.ether=l/5, v/v) to give the product 8 (10.0 g, 47% yield) as a white solid. [0308] 1H NMR (400 MHz, CDC13): 8.19 (s, 2H), 7.38-7.25 (m, 10H), 5.05 (s, 2H), 4.76-4.68 (m, 1H), 4.43 (s, 2H), 3.82-3.75 (m, 1H), 2.87-2.81 (m, 2H), 2.24-2.17 (m, Synthesis of 2-(3-hydroxycyclobutoxy)pyrimidin-5-ol [0309] To the mixture of 8 (8.84 g, 24.42 mmol) in dry DCM (250 mL) was added BC13 (100 mL, 1M in DCM, 0.1 mol) at -20 C under N2. The resulting mixture was stirred further 0.5 h at -20 C . TLC showed the reaction was completed, and then it was quenched by the addition of MeOH (20 mL). The solvent was removed in vacuo to give the crude product. It was diluted with DCM (50 ml) and the solid was filtered out by filtration. The cake was suspended in H20 (20 mL) and filtered, dried in vacuo to give the product (2.2 g, 50% yield) as a white solid. [0310] 1H NMR (400 MHz, DMSO-d6): 9.76 (s, 1H), 8.12 (s, 2H), 5.07 (br, 1H), 4.59-4.52 (m, 1H), 3.85-3.78 (m, 1H), 2.76-2.72 (m, 2H), 1.91-1.85 (m, 2H). LCMS [mobile phase: from 50% water (0.1% TFA) and 50% CH3CN to 5% water (0.1% TFA) and 95% CH3CN in 6.0 min, finally under these conditions for 0.5 min.] purity is >95%, Rt = 1.84 min; MS Calcd.: 182.2; MS Found: 183.1

At the same time, in my other blogs, there are other synthetic methods of this type of compound,100058-61-5, 3-(Benzyloxy)cyclobutanol, and friends who are interested can also refer to it.

Reference:
Patent; TRIUS THERAPEUTICS INC.; LAWRENCE LIVERMORE NATIONAL SECURITY, LLC; BENSEN, Daniel; BORCHARDT, Allen; CHEN, Zhiyong; FINN, John, M.; LAM, Thanh, To; LEE, Suk, Joong; LI, Xiaoming; TARI, Leslie, William; TENG, Min; TRZOSS, Michael; ZHANG, Junhu; JUNG, Michael, E.; LIGHTSTONE, Felice, C.; WONG, Sergio, E.; NGUYEN, Toan, B.; WO2014/43272; (2014); A1;,
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