Category: alcohols-buliding-blocks

Reference of 623-04-1, 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. 623-04-1, name is (4-Aminophenyl)methanol. A new synthetic method of this compound is introduced below.

To 4.97 g (40.35 mmol) of 4-aminobenzylalcohol dissolved in 30 mL of was added 9.69 g (44.39 mmol) of di-tert-butyl dicarbonate. The mixture was stirred at room temperature overnight, partitioned between ethyl acetate and water, dried over magnesium sulfate and concentrated to provide 8.4 g t-butyloxycarbonyl-protected 4-aminobenzyl alcohol, as a colorless solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,623-04-1, (4-Aminophenyl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; Bamberg, Joe Timothy; Gabriel, Tobias; Krauss, Nancy Elisabeth; Mirzadegan, Taraneh; Palmer, Wylie Solang; Smith, David Bernard; US2004/77646; (2004); A1;,
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Application of 534-03-2, 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. 534-03-2, name is 2-Aminopropane-1,3-diol. A new synthetic method of this compound is introduced below.

The synthetic steps taken in this embodiment are as follows:Preparation of 5-dimethylamino-1,3-dioxan-2-one:After dissolving 19.97 g of serinol in 50 mL of formic acid, 40 mL of a 37% (w/v) formaldehyde solution was added, and the mixture was heated to 120 C for 8 hours, and then cooled to room temperature. After removing excess formic acid, formaldehyde and water from the product by a rotary evaporator, the product was evaporated to dryness with anhydrous magnesium sulfate. The filtrate was collected by filtration and subjected to distillation under reduced pressure. The fraction of 108-109 C was collected under a vacuum of 2 mbar, and crystallized at -20 C to obtain a pale intermediate in a yield of 63.6%. Characterization by infrared spectroscopy (FT-IR) and nuclear magnetic resonance spectroscopy (1H NMR) confirmed that the pale intermediate was 2-dimethylamino-1,3-propanediol.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,534-03-2, its application will become more common.

Reference:
Patent; Guangdong Microbiology Institute (Guangdong Microbiology Analysis To Detect Center); Dong Peng; Xie Xiaobao; Gan Shuzhao; Shi Qingshan; (8 pag.)CN109467547; (2019); A;,
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Related Products of 702-82-9, 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.702-82-9, name is 3-Aminoadamantan-1-ol, molecular formula is C10H17NO, molecular weight is 167.2481, as common compound, the synthetic route is as follows.

In a clean round bottom flask, (100gm) of 1-amino-3-adamantol in l000ml of acetonitrile were charged. 239.8gm of potassium carbonate was charged to the above flask. The reaction mass was heated to 82-85C. The compound of formula III (4x25gm), was charged after 60-90 mm intervals. After completion of reaction, the reaction mass was cooled to 65-70C. The reaction mass was filtered and the solid was washed with 500m1 acetonitrile and suck dried. Theacetonitrile was distilled out from filtrate under vacuum at 50-55C. Ethyl acetate was charged to the residue and the slurry stirred at 50-55C for 30-45 minutes. The slurry was cooled to 20-30C and stirred for 60-90 minutes. The solid was filtered and washed with ethyl acetate and suck dried, The wet cake was suspended in IPA and heated to 80-85C to get a clear solution. The clear solution was charcoalised and filtered through hyflo. The filtrate was distilled oUt undervacuum to get final volume to 5Volume. The reaction mass was cooled to -5 to 5C and stirred for 60-90 minutes. The solid was filtered and washed with IPA and suck dried. The solid was dried under vacuum at 50-55C. 105 to 120gm of solid was obtained (yield 59-68%, HPLC purity >98%)

The chemical industry reduces the impact on the environment during synthesis 702-82-9, I believe this compound will play a more active role in future production and life.

Reference:
Patent; GLENMARK PHARMACEUTICALS LIMITED; GLENMARK GENERICS LIMITED; BHIRUD, Shekhar Bhaskar; BHUSHAN, Kumar Hari; THANEDAR, Amit Anant; RAUT, Changdev Namdev; CHAND, Prem; WO2014/102815; (2014); A1;,
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Application of 148043-73-6, 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.148043-73-6, name is 4,4,5,5,5-Pentafluoropentan-1-ol, molecular formula is C5H7F5O, molecular weight is 178.1, as common compound, the synthetic route is as follows.

To a stirred solution of Jones reagent (20 ml, 160 mmol) in acetone (20 ml), cooled in an ice bath, a solution of 4,4,5,5,5-pentafluoro-1-pentanol (7.12 g, 40 mmol) in acetone (30 ml) was added dropwise. After remaining ice bath, the mixture was stirred continuously at room temperature for 1 h. The mixture was poured into ice/water and extracted with diethyl ether. Crude ether was extracted with aqueous 2 N sodium hydroxide. On the inorganic layer was acidified with aqueous 6 N hydrochloric acid and the organic layer was extracted with diethyl ether. The final extract was washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give crude 4,4,5,5,5-pentafluoropentanoic acid as colorless liquid (6.31 g, 82%), which was used in the next step without further purification. [01445] 1H NMR (300 MHz, CDCl3) delta: 11.5-9.5 (1H, br.s, CO2H), 2.70 (2H, t, J=7.8 Hz, C2-H), 2.53-2.33 (2H, m, C3-H).

Statistics shows that 148043-73-6 is playing an increasingly important role. we look forward to future research findings about 4,4,5,5,5-Pentafluoropentan-1-ol.

Reference:
Patent; Chugai Seiyaku Kabushiki Kaisha; US6645951; (2003); B1;,
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In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 5617-32-3, name is 3,6,9,12,15,18-Hexaoxaicosane-1,20-diol, the common compound, a new synthetic route is introduced below. Product Details of 5617-32-3

General procedure: (Using the synthesis of macrocyclic sulfate 6a as an example). To a stirring solution of tetra(ethylene glycol) 5a (40.0 g, 205.95 mmol), triethylamine (100.73 g, 988.56 mmol), and DMAP (1.26 g, 10.30 mmol) in CH2Cl2 (3 L) at 0 ¡ãC was slowly added a solution of SOCl2 (50.30 g, 411.90 mmol, in 50 mL CH2Cl2). After the addition, the stirring mixture was warmed to 25 ¡ãC and monitored with TLC until the complete consumption of tetra(ethylene glycol). The reaction was quenched with 1.5 L water. The organic layer was collected, filtrated through a pad of silica gel, and concentrated under vacuum to provide the macrocyclic sulfite intermediate as brownish oil which was used directly in the next step. To the solution of macrocyclic sulfite in a mixture of CH2Cl2 (200 mL), CH3CN (200 mL), and water (300 mL) at 0 ¡ãC was added NaIO4 (52.86 g, 247.14 mmol) and RuCl3?3H2O (0.27 g, 1.03 mmol). The stirring mixture was gradually warmed to 25 ¡ãC and monitored with TLC. Upon complete consumption of the macrocyclic sulfite, the reaction mixture was filtered through a pad of Celite. Organic layer was collected, washed with brine, concentrated under vacuum, and recrystallized in methanol at -20 ¡ãC to afford the macrocyclic sulfate 6a as clear crystal (25.14 g, 47percent yield).

The synthetic route of 5617-32-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Deng, Tao; Mao, Xianglan; Xiao, Yan; Yang, Zhigang; Zheng, Xing; Jiang, Zhong-Xing; Bioorganic and Medicinal Chemistry Letters; vol. 29; 4; (2019); p. 581 – 584;,
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Related Products of 115-20-8, 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 115-20-8 as follows.

To a suspension of 7-acetoxycoumarin-4-acetic acid 5 (945 mg, 3.6 mmol, 1 eq) in 47 mL of anhydrous dichloromethane at room temperature under nitrogen was added 2,2,2-trichloroethanol (431 muL, 4.5 mmol, 1.25 eq). A solution of Lambda^Lambdaf’-dicyclohexylcarbodiimide (818 mg, 4 mmol, 1.1 eq) in 10 mL of anhydrous dichloromethane was added. The reaction mixture was stirred for 15 min, after which it was diluted with dichloromethane and filtered. The filtrate was concentrated under vacuum. Column chromatography on silica gel (CH2Cl2 then CH2Cl2^tOAc, 10:1) afforded product 6a (1.37 g, 96 %): Rf 0.78 (CH2Cl2:Et0Ac, 5:1); 1H NMR (300 MHz, CDCl3): delta 7.61 (d, 1 H, J5,6 8.7 Hz, H-5), 7.15 (d, 1 H, J6,8 2.1 Hz, H-8), 7.07 (dd, 1 H, J6,8 2.3, J5,6 8.7 Hz, H-6), 6.42 (s, 1 H, H-3), 4.77 (s, 2 H, CH2CCl3), 3.91 (2 s, 2 Eta, CH2CO2), 2.33 (s, 3 Eta, OAc); 13C NMR (75 MHz, CDCl3): delta 168.6, 167.0, 154.5, 153.5, 146.5, 125.5, 118.5, 117.0, 116.5, 110.9, 74.6, 37.7, 21.2; ESI-MS: m/z 393 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,115-20-8, its application will become more common.

Reference:
Patent; UNIVERSITY OF WASHINGTON; GELB, Michael, H.; BLANCHARD, Sophie; WO2010/81163; (2010); A2;,
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Electric Literature of 41790-30-1, 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. 41790-30-1, name is (5,6,7,8-Tetrahydronaphthalen-1-yl)methanol, molecular formula is C11H14O, 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.

Step 2 – Tetralin-5-carbaldehyde (0543) [00350] To a solution of tetralin-5-ylmethanol (7.20 g, 44.3 mmol) in dichloromethane (100 mL) was added manganese dioxide (19.2 g, 221 mmol) under a nitrogen atmosphere. The mixture was stirred at 20 C for 6 hrs. On completion, the mixture was filtered; the filtrate was concentrated in vacuo to afford a residue. The residue was purified with silica gel chromatography (petroleum ether:ethyl acetate = 20:1) to afford the title compound. 1H NMR (400MHz, DMSO-d6) delta = 10.23 (s, 1H), 7.65 (dd, J = 1.1, 7.4 Hz, 1H), 7.41 – 7.35 (m, 1H), 7.35 – 7.29 (m, 1H), 3.15 (t, J = 6.1 Hz, 2H), 2.79 (t, J = 6.0 Hz, 2H), 1.79 – 1.69 (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 41790-30-1, (5,6,7,8-Tetrahydronaphthalen-1-yl)methanol.

Reference:
Patent; RAZE THERAPEUTICS, INC.; MAINOLFI, Nello; MOYER, Mikel P.; SAIAH, Eddine; (264 pag.)WO2017/156181; (2017); A1;,
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Synthetic Route of 928-92-7, 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 928-92-7 as follows.

Example 5; Methyl 5-methyl-3,4-dihydro-2H-pyrano [2,3-c] pyridine-6-carboxylate(a) (is)-Methyl 2-((2-(hex-4-en-l-yloxy)-2-oxoethyl)amino)-2-oxoacetateTo a vessel maintained at 40 ¡ãC was charged CDI (2.75 g, 0.95 eq) and TBME (9 mL). To this mixture was added with stirring a solution of N-(?-butoxycarbonyl)glycine (3.1 g, 1.0 eq) dissolved in TBME (12 mL) over 30 min. Stirring was continued for an additional 30 min, whereupon trans-4-hexen-l-ol (1.7 g, 0.95 eq) was added over 30 min. The mixture was maintained with stirring at 40 ¡ãC for an additional 3.5 h, then cooled to ambient temperature and stirred a further 14 h. The mixture was washed with IN HQ (2 x 7.8 mL) then water (1 x 7.8 mL). The organic layer was dried over a2S04, filtered and concentrated to give (.pound.)-hex-4-en-l-yl 2-((tert-butoxycarbonyl)amino)acetate as an oil. The oil was dissolved in DCM (12 mL) and 4.0 M HC1 in dioxane (2.8 mL) was added drop-wise. The mixture was stirred at ambient temperature for 1.5 h then the mixture was heated to 35 ¡ãC and stirred for 3 h. 4.0 M HC1 in dioxane (2.8 mL) was added drop-wise. After 6 h at 35 ¡ãC a further dose of 4.0 M HC1 in dioxane (2.8 mL) was added drop-wise and the mixture was stirred for a further 4 h. The mixture was cooled to ambient temperature and the solvent was removed under reduced pressure. A portion of the residue (1.0 g) was dissolved in DCM (8 mL) and methyl 2-chloro-2-oxoacetate (0.63 g) was added. Triethylamine (1.0 g) was added drop-wise over 20 min. The mixture was stirred for 1 h before being quenched by IN HC1 (2.5 mL) to form a biphasic mixture. The layers were separated and the organic layer was washed with IN HCl (1 x 2.5 mL), water (1 x 2.5 mL) and concentrated under reduced pressure to provide an oil. Flash columnchromatography (S1O2, 10->60percent EtO Ac/Hex gradient) provided the title compound as an oil as a 95:5 mixture of trans:cis isomers. XH NMR (300 MHz, CDCI3) delta ppm 7.57 (s, 1 H), 5.31-5.55 (m, 2 H), 4.17 (t, J=6.69 Hz, 2 H), 4.12 (d, J=5.51 Hz, 2 H), 3.92 (s, 3 H), 1.97-2.10 (m, 2 H), 1.67-1.77 (m, 2 H), 1.62-1.67 (m, 3 H); 13C NMR (75 MHz, CDCI3) delta ppm 168.60, 160.35, 156.28, 129.49, 126.12, 65.34, 53.68, 41.47, 28.62, 28.17, 17.84; HRMS (M+H) m/z, calcd for CnH18N05, 244.1185; found 244.1 187.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,928-92-7, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; SISKO, Joseph; MANS, Douglas; YIN, Hao; WO2012/12391; (2012); A2;,
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Application of 1208434-90-5 , The common heterocyclic compound, 1208434-90-5, name is (2,6-Difluoro-3,5-dimethoxyphenyl)methanol, molecular formula is C9H10F2O3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

To a solution of (2,6-difluoro-3,5-dimethoxyphenyl)methanol (1.5g, 7.38mmol) in diethyl ether (20mL), and pyridine (0.029g, 0.3mmol), PBr3 (0.69mL, 7.38mmol) was added slowly over a period of 10 min. Reaction mass was stirred at 35 C for 3hr. Reaction mass was quenched with ice cold water and extracted with diethyl ether (3x25mL). The organic phase was washed with brine, dried over Na2S04, filtered and concentrated under vacuum. The residue was purified by silica gel column chromatography to afford the title compound (1.68g, yield: 85.2%). 1H-NMR (CDC13, 300MHz): 6.60 (t, 1H), 4.52 (s, 2H), 3.87 (s, 6H).

The synthetic route of 1208434-90-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EISAI R & D MANAGEMENT CO., LTD.; REYNOLDS, Dominic; HAO, Ming-Hong; WANG, John; PRAJAPATI, Sundeep; SATOH, Takashi; SELVARAJ, Anand; (128 pag.)WO2016/164703; (2016); A1;,
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Adding a certain compound to certain chemical reactions, such as: 1072-52-2, 2-(Aziridin-1-yl)ethanol, 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, 1072-52-2, blongs to alcohols-buliding-blocks compound. Computed Properties of C4H9NO

Example 20 (Scheme 15): Preparation of 2-((2-bromoethyl)-2-{ll-[2-((2-bromoethyl){2- [(methylsulfonyl)oxy] ethyl} amino)-3,5-dinitrophenyl] -6-hydroxy-6-oxido-ll-oxo-5,7- dioxa-2,10-diaza-6-phosphaundec-l-anoyl}-4,6-dinitroanilino)ethyl methanesulfonate(52); Reaction of 37 as in Scheme 15 gave 2-((2-bromoethyl)-2-{l l-[2-((2-bromoethyl){2- [(methylsulfonyl)oxy]ediyl}arnino)-3,5-dinitrophenyl]-6-oxido-ll-oxo-5,7-dioxa-2,10-diaza-6- phosphaundec-l-anoyl}-4,6-dinitroanilino)ethyl methanesulfonate (51) as a yellow oil: 1H NMR [(CDj)2SO] delta 8.99 (t, / = 5.6 Hz, 2 H), 8.75 (d, / = 2.8 Hz, 2 H), 8.40 (d, / = 2.8 Hz, 2 H), 6.98 (dj = 709 Hz, 1 H), 4.28 (t,/ = 5.5 Hz, 4 H), 4.20 (m, 4 H), 3.58 (m, 8 H), 3.48 (m, 8 H), 3.13 (s, 6 H); 13C NMR delta 165.5, 145.9, 145.3, 140.9, 135.6, 127.6, 122.4, 67.4, 63.4, 54.3, 51.1, 39.7, 36.4, 29.7; HRMS (FAB) calcd for C28H3879Br2N8O19PS2 [M+H]+ m/Z 1042.9799; found 1042.9786.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1072-52-2, its application will become more common.

Reference:
Patent; AUCKLAND UNISERVICES LIMITED; WO2008/30112; (2008); A1;,
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