200004-39-3Relevant academic research and scientific papers
A method for preparing optically active 3-amino-1-phenylpropanol derivatives as an intermediate and a method for preparing optically active pharmaceutical products using the same
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Paragraph 0181-0183, (2016/11/09)
The present invention relates to a method for preparing a 3-amino-1-phenylpropanol derivative having (R) or (S) optical activity with 80% or more of an enantiomeric excess (ee), which includes a step of performing an asymmetric reduction reaction in the presence of a spiroborate ester catalyst and a hydrogen donor. The invention also relates to a method for preparing an optically active pharmaceutical product, which includes a step of preparing a (R)- or (S)-3-amino-1-phenylpropanol derivative, that is an intermediate, by using the catalyst.(AA) 3-amino-1-phenylpropanol(BB) Tomoxetine(CC) Nisoxetine(DD) FluoxetineCOPYRIGHT KIPO 2016
Lipase-catalyzed synthesis of both enantiomers of 3-chloro-1-arylpropan-1- ols
Pop, Laura Ancua,Czompa, Andrea,Paizs, Csaba,Toa, Monica Ioana,Vass, Elemer,Matyus, Peter,Irimie, Florin-Dan
, p. 2921 - 2928 (2011/10/13)
The lipase-catalyzed synthesis of both enantiomers of 3-chloro-1-(4- fluorophenyl)propan-1-ol, 3-chloro-1-(4-iodophenyl)propan-1-ol, and 3-chloro-1-phenylpropan-1-ol is described. The procedure is based on the enantiomer-selective acylation of the racemic alcohols in presence of lipase from Pseudomonas fluorescens (LAK) followed by the lipase from Candida rugosa (CRL) mediated hydrolysis of previously obtained enantiomerically enriched 1-aryl-3-chloropropyl esters. For the production of enantiopure (S)-1-aryl-3-chloropropan-1-ols (99% ee, 34-42% yield) the reactions were stopped at higher conversions than the theoretical optimum of 50%, while for enantiopure (R)-1-aryl-3-chloropropyl acetates (99% ee) the reactions were stopped at lower conversions. The latter compounds were enzymatically hydrolyzed into the corresponding (R)-1-aryl-3-chloropropan-1-ols (97-99% ee, 18-24% yield). The absolute configuration of the resolution products was determined by VCD measurements combined with quantum chemical calculations. Georg Thieme Verlag Stuttgart - New York.
Ezetimibe analogs with a reorganized azetidinone ring: Design, synthesis, and evaluation of cholesterol absorption inhibitions
Xu, Xianxiu,Fu, Renzhong,Chen, Jin,Chen, Shengwu,Bai, Xu
, p. 101 - 104 (2007/10/03)
The underlying principle of drug design in this paper is that the maximum retention of the functional groups that exist in the marketed drug would provide a higher probability for comparable safety while the conformational changes in the newly created ana
Highly enantioselective reduction of achiral ketones with NaBH4/Me3SiCl catalyzed by (S)-α,α-diphenylpyrrolidinemethanol
Jiang, Biao,Feng, Yan,Zheng, Jian
, p. 10281 - 10283 (2007/10/03)
The reducing agent prepared from sodium borohydride, trimethylsilyl chloride and a catalytic amount of (S)-α,α-diphenylpyrrolidinemethanol has been successfully applied to the enantioselective reduction of ketones. The optically active secondary alcohols were obtained in excellent enantiomeric excess and almost quantitative chemical yield. (C) 2000 Elsevier Science Ltd.
Asymmetric Synthesis of 2-Aryl Substituted Oxetanes by Enantioselective Reduction of β-Halogenoketones using Lithium Borohydride modified with N,N'-Dibenzoylcystine
Soai, Kenso,Niwa, Seiji,Yamanoi, Takashi,Hikima, Hitoshi,Ishizaki, Miyuki
, p. 1018 - 1019 (2007/10/02)
Optically active 2-aryl substituted oxetanes are synthesised in high enantiomeric excesses (up to 89percent e.e.) via enantioselective reduction of β-halogenoketones with lithium borohydride using (R,R')-N,N'-dibenzoylcystine and t-butyl alcohols as ligands.
