Resolution of 3-(methylamino)-1-(2-thienyl)propan-1-ol, a new key intermediate for duloxetine, with (S)-mandelic acid

被引：27

作者：

Sakai, K ^{[1
]}

Sakurai, R

Yuzawa, A

Kobayashi, Y

Saigo, K

机构：

[1] Yamakawa Chem Ind Co Ltd, R&D Div, Kitaibaraki 3191541, Japan

[2] Univ Tokyo, Grad Sch Engn, Dept Chem & Biotechnol, Tokyo 1138656, Japan

来源：

TETRAHEDRON-ASYMMETRY | 2003年 / 14卷 / 12期

关键词：

D O I：

10.1016/S0957-4166(03)00315-X

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The resolution of racemic 3-(methylamino)-1-(2-thienyl)propan-1-ol 3, a new key intermediate for duloxetine 1, was studied. The conditions were optimized for an industrial-scale resolution of 3 by using (S)-mandelic acid 4 as a resolving agent and 2-butanol containing 2 equimolar amounts of water as a solvent. The (S)-3.(S)-4.H2O diastereomeric salt was crystallized to give pure (S)-3 with >99.9% e.e. after liberation of the amine. The absolute configuration of liberated (-)-3 was determined as (S) by X-ray crystallography. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

页码：1631 / 1636

页数：6

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