Category: alcohols-buliding-blocks

Electric Literature of 111-46-6, 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 111-46-6, name is 2,2′-Oxybis(ethan-1-ol). This compound has unique chemical properties. The synthetic route is as follows.

Sodium metal (64 mg, 0.03 eq) was added to a solution of diethylene glycol (29.5 g, 0.278 mmol) in THF (100 mL). The mixture was stirred for 1 hour to dissolve the sodium, then /cvV-butyl acrylate (12.4 g, 97 mmol) was added. The resulting mixture was stirred for 2 days, then concentrated under reduced pressure and the residue purified by silica chromatography (1 : 1 hexane:EtOAc) to give the title compound (9.1 g, 40%) as a colorless oil. (0315) [00139] NMR (400 MHz, CDCb): d 3.75 (m, 4H), 3.64 (m, 6H), 2.53 (t, 2H), 2.40 (s, 1H), (0316) 1.45 (s, 9H).

According to the analysis of related databases, 111-46-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DANA-FARBER CANCER INSTITUTE, INC.; GRAY, Nathanael S.; SCOTT, David; LI, Zhengnian; PINCH, Benika J.; OLSON, Calla; FISCHER, Eric S.; NOWAK, Radoslaw P.; DONOVAN, Katherine A.; (171 pag.)WO2020/69105; (2020); A1;,
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Reference of 108343-90-4 , The common heterocyclic compound, 108343-90-4, name is 2-Amino-2-(2-methoxyphenyl)ethanol, molecular formula is C9H13NO2, 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.

In a 250-ml triple-neck flask, 4.2 g (25 mmol) of 2-amino-2-(2-methoxyphenyl)ethanol obtained previously and 2.5 g (25 mmol) of KHCO3 are solubilized in 40 ml of water. After 10 min of stirring, it cooled to 0 C. and 3.4 g (25 mmol) of K2CO3, are added and then 17 ml (32.6 mmol) of 20% phosgene in toluene are added dropwise. The medium is stirred at 0 C. for 6 h. The formation of a white product is observed, which is filtered and dried. 3.6 g (18.6 mmol) of 4-(2-methoxyphenyl)oxazolidin-2-one are recovered in the form of a white solid. Yield: 75% . 1H NMR (CDCl3) delta: 3.85 (s, 3H); 4.18 (dd, 1H, J=8.8 and 6.4 Hz); 4.80 (m, 1H); 5.25 (dd, 1H, J=8.6 and 6.4 Hz); 5.46 (is, 1H); 6.90 (m, 1H); 7.01 (m, 1H); 7.32 (m, 2H).

The synthetic route of 108343-90-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PIERRE FABRE MEDICAMENT; SOKOLOFF, Pierre; MAILLOS, Philippe; CUISIAT, Florence; VIDALUC, Jean-Louis; IMBERT, Thierry; US2015/336943; (2015); A1;,
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Synthetic Route of 37585-16-3, 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.37585-16-3, name is (2-Amino-4-chlorophenyl)methanol, molecular formula is C7H8ClNO, molecular weight is 157.6, as common compound, the synthetic route is as follows.

4-chloro-2- (3-fluoro-benzyloxy)-7-methoxy-quinazoline (3.18, 10 mmol) and 4-chloro-2-amino-benzyl alcohol (1.57 g, 10 mmol) were dissolved in isopropanol (30 ml) to form a solution, and phosphoric acid (0.20 ml) was added dropwise to the solution. The reaction was carried out according to General Method I for preparing the intermediate III to obtain a white solid intermediate M-35 (3.83 g, 80.63%).

The chemical industry reduces the impact on the environment during synthesis 37585-16-3, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Shenzhen Salubris Pharmaceuticals Co., Ltd.; Shanghai Institute of Pharmaceutical Industry; LI, Jianqi; ZHANG, Zixue; XIE, Peng; ZHANG, Qingwei; EP2592083; (2013); A1;,
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Electric Literature of 59854-12-5, 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. 59854-12-5, name is tert-Butyl 4-hydroxybutanoate, molecular formula is C8H16O3, 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.

To a solution of tert-butyl 4-hydroxybutanoate (56 mg, 0.35 mmol) in 1 mL DCM was added DMP (273 mg, 0.64 mmol, 1.8 eq) and the solution was stirred for 2 h at rt. The reaction mixture was diluted with DCM and washed 3X with 10% sodium thiosulfate solution and once with saturated sodium bicarbonate solution to yield 30 mg crude tert-butyl 4- oxobutanoate (54% crude yield). Crude free-base norheroin 2 (25 mg, 0.07 mmol) was dissolved in 4 mL of dry 1,2-dichloroethane, followed by the addition of crude ferf-butyl 4- oxobutanoate (30 mg, 0.19 mmol, 2.7 eq) and NaBH(OAc)3(22 mg, 0.11 mmol, 1.5 equiv). The reaction solution was allowed to stir for 2 h. The reaction mixture was diluted with DCM and washed twice with saturated sodium bicarbonate solution. Purification proceeded via preparative TLC using 5% MeOH in EtOAc as an eluent to yield 4.3 mg of 9 (12% yield).

According to the analysis of related databases, 59854-12-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THE SCRIPPS RESEARCH INSTITUTE; JANDA, Kim, D.; (41 pag.)WO2019/94528; (2019); A1;,
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Adding a certain compound to certain chemical reactions, such as: 722-92-9, 2-(4-Aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol, 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, 722-92-9, blongs to alcohols-buliding-blocks compound. COA of Formula: C9H7F6NO

2-(tert-Butoxycarbonyl)-5-(methylsulfonyl)isoindoline- 1 -carboxylic acid (4.40 g, 12.89 mmol) and 2-(4-aminophenyl)- 1,1,1,3,3,3 -hexafluoropropan-2-ol (3.34 g, 12.89 mmol)were combined in EtOAc (50 mL) to give a suspension, before the addition of triethylamine (5.39 mL, 38.67 mmol) gave a dark brown solution. The solution was chilled by stirring on an ice I water bath before the addition of T3P (50percent in EtOAc, 15.35 mL, 25.78 mmol) through a dropping funnel. The addition was controlled to ensure that the temperature did not exceed 5 ¡ãC. After one hour the reaction solution was washed withwater (2 x 5OmL). The combined water washes were extracted with EtOAc (5OmL). The combined organic extracts were washed with 0. 1M aq HC1 (2 x 5OmL) and brine (25mL) before being dried over MgSO4. Filtration and concentration in vacuo gave a residue, which was purified by flash chromatography eluting with 0 ? 60percent EtOAc in n-heptane to give the title compound (4.95 g, 66percent) as a solid.LCIMS: mlzrr 581 EM-H]-. ?H NMR (400 MHz, DMSO-d6, mixture of rotamers, 1.8*:1) 151.35*, 1.47 (s, 9H), 3.20, 3.21* (s, 3H), 4.69? 4.88 (m, 2H), 5.61*, 5.63 (s, 1H), 7.6?7.76 (m, 5H), 7.86?7.92 (m, 1H), 7.98, 8.01* (s, 1H), 8.63*, 8.65 (s, 1H), 10.75 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,722-92-9, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; LEVER, Sarah; NARJES, Frank; OLSSON, Roine, Ingemar; VON BERG, Stefan; (124 pag.)WO2018/229155; (2018); A1;,
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Adding a certain compound to certain chemical reactions, such as: 431-38-9, 3-Amino-1,1,1-trifluoropropan-2-ol, 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, Application In Synthesis of 3-Amino-1,1,1-trifluoropropan-2-ol, blongs to alcohols-buliding-blocks compound. Application In Synthesis of 3-Amino-1,1,1-trifluoropropan-2-ol

General procedure: To a stirred solution of amino alcohol 5 (8.80 mmol, 1.10 equiv.) in DMF (16.0 mL, 0.5M) atroom temperature was added isothiocyanate 4 (8.00 mmol, 1.00 equiv.). After stirring for 2minutes at room temperature, Vilsmeier salt 3 (12.00 mmol, 1.50 equiv.) and iPr2NEt (12.00mmol, 1.50 equiv.) were added sequentially. The reaction mixture was allowed to stir at 75Cuntil adjudged complete by TLC, generally 4 hours. The reaction was diluted with EtOAc(50mL) and sequentially washed with sat. aq. NaHCO3 (25mL) and brine (25mL). The organiclayer was dried over MgSO4, polish filtered, and concentrated under reduced pressure. The cruderesidue was purified by silica gel column chromatography (100% heptane to 80% EtOAc inheptane gradient) to give 6.

The synthetic route of 431-38-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Corbett, Michael T.; Caille, Seb; Synlett; vol. 28; 20; (2017); p. 2845 – 2850;,
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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.33036-62-3, name is 4-Bromo-1-butanol, molecular formula is C4H9BrO, molecular weight is 153.0177, as common compound, the synthetic route is as follows.Recommanded Product: 4-Bromo-1-butanol

PREPARATION 9 1-Tetrahydropyranyloxy-4-bromobutane (Formula XIII: A is trimethylene). Concentrated hydrobromic acid (75 drops of 48%) is added with stirring to a mixture of 4-bromobutanol (150 ml.) and dihydropyran (300 ml.) at 0. This mixture is stirred and allowed to warm slowly to 25 C. during 15 hours. Evaporation under reduced pressure gives a residue which is divided into two equal parts, each part being chromatographed on 1.5 kg. of silica gel, each column being eluted with 7.5 l. of 5% ethyl acetate in Skellysolve B, and then with 4 l. of 7.5% ethyl acetate in Skellysolve B, collecting 500 ml. fractions. Fractions 5-11 from each column are evaporated to give a total of 240 g. of 1-tetrahydropyranyloxy-4-bromobutane.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,33036-62-3, 4-Bromo-1-butanol, and friends who are interested can also refer to it.

Reference:
Patent; The Upjohn Company; US4008263; (1977); A;,
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Application of 109-83-1, 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 109-83-1, name is 2-(Methylamino)ethanol. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 4.15 g (55.5 mmol) NaHSO3, 8 mL of water, 0.78 g (4.19 mmol) of 1-(6-hydroxy-2-naphthyl)-1-ethanone (prepared as described in Example 1(b)), and 8 mL of 2-methylaminoethanol was heated and stirred in a steel bomb at 140 C. for 28 hours. After cooling, the mixture was distributed between ethyl acetate and water (500 mL and 200 mL, respectively). The organic layer was dried and evaporated to leave raw 1-(6-(2-hydroxyethyl-methylamino)-2-naphthyl)-1-ethanone (0.749 g, 73%) of which was further purified by radial chromatography (4 mm SiO3, CH2Cl2).

According to the analysis of related databases, 109-83-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; The Regents of the Univ. of California; US6274119; (2001); B1;,
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Adding a certain compound to certain chemical reactions, such as: 1205037-95-1, trans-3-Aminocyclobutanol hydrochloride, 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, Safety of trans-3-Aminocyclobutanol hydrochloride, blongs to alcohols-buliding-blocks compound. Safety of trans-3-Aminocyclobutanol hydrochloride

General Method C (Amine substitution) A solution of benzoimidazol-2-yl arylpyridinone bistriflate derivate (1 equiv) in MeCN, DCM, or DMF was treated with amine (1.2-3 equiv). In the case where the amine is a salt (e.g. HCl), the amine salt was dissolved in MeOH or DMF and passed through a PoraPak Rxn CX ion exchange column to yield the free base which was added to the reaction mixture. The reaction mixture was stirred at rt or up to 45 C for 1-48 h. Solvent was removed and the crude product was purified by column chromatography or prep-HPLC to give the desired product. General Method D (Global deprotection) A solution of protected benzoimidazol-2-yl arylpyridinone derivate (1 equiv) in TFA/conc. HCl (7: 1 v/v) was heated at 80-100 C for 3-24 h. Solvent was removed and the crude product was purified by column chromatography (free base) or prep-HPLC (TFA salt) to give the desired product. To generate the desired product as a HCl salt, the free base was dissolved in MeOH and 1 M HCl-Et20 (2-4 equiv) was added at rt. The solution was stirred for 5 min and azeotroped twice with MeOH.

The synthetic route of 1205037-95-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITY HEALTH NETWORK; SAMPSON, Peter Brent; PATEL, Narendra Kumar B.; PAULS, Heinz W.; LI, Sze-Wan; NG, Grace; LAUFER, Radoslaw; LIU, Yong; LANG, Yunhui; (93 pag.)WO2016/205942; (2016); A1;,
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Adding a certain compound to certain chemical reactions, such as: 13330-96-6, 4-(Dimethylamino)butan-1-ol, 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, Recommanded Product: 4-(Dimethylamino)butan-1-ol, blongs to alcohols-buliding-blocks compound. Recommanded Product: 4-(Dimethylamino)butan-1-ol

General procedure: To a solution of 6-substituted pyridazinone 9 (0.5 mmol) in DMF (10 mL) was added Cs2CO3 (0.55 mmol). An appropriately substituted nitro benzyl chloride (0.52 mmol) was added and the resulting mixture was stirred at 40-50 C for 3 h, the solvent was removed under reduced pressure and the residue was dissolved in EtOAc (30 mL), which was then washed with brine (3 ¡Á 10 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo. The crude product, 2-nitrobenzyl-6-substituted-pyridazin-3(2H)-one (10), was used in the next step without further purification. To a solution of 10 in 95 % ethanol (50 mL) was added acetic acid (10 mmol) followed by slow addition of iron powder (2 mmol). The resulting mixture was stirred for 5 h at 100 C. The mixture was then filtered through celite and the filter cake was washed with 95 % ethanol (3 ¡Á 15 mL). The combined ethanol filtrates were evaporated in vacuo and the residue was re-dissolved in ethyl acetate (30 mL). The organic layer was washed with brine (3 ¡Á 10 mL) and 2 M NaOH (10 mL) sequentially. The organic layer was dried over anhydrous Na2SO4, evaporated in vacuo to afford 2-aminobenzyl-6-substituted-pyridazin-3(2H)-one (11) as a yellow solid, which was used without further purification. To a stirred solution of 11 and triphosgene (1 mmol) in dry dichloromethane (5 mL) was added triethylamine (2 mmol) under nitrogen atmosphere. A solution of the corresponding alcohol (1 mmol) in dichloromethane (5 mL) was added 5-10 min later and the mixture was stirred at room temperature overnight, diluted with dichloromethane (15 mL) and washed with water (3 ¡Á 20 mL). The organic phases were separated, combined, dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by using column chromatography to afford the corresponding product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,13330-96-6, 4-(Dimethylamino)butan-1-ol, and friends who are interested can also refer to it.

Reference:
Article; Xing, Weiqiang; Ai, Jing; Jin, Shiyu; Shi, Zhangxing; Peng, Xia; Wang, Lang; Ji, Yinchun; Lu, Dong; Liu, Yang; Geng, Meiyu; Hu, Youhong; European Journal of Medicinal Chemistry; vol. 95; (2015); p. 302 – 312;,
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