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Resolution of 3-(methylamino)-1-(2-thienyl)propan-1-ol, a new key intermediate for duloxetine, with (S)-mandelic acid
Tetrahedron: Asymmetry Pub Date : 20 June 2003 , DOI: 10.1016/s0957-4166(03)00315-x Kenichi Sakai , Rumiko Sakurai , Atsushi Yuzawa , Yuka Kobayashi , Kazuhiko Saigo
Tetrahedron: Asymmetry Pub Date : 20 June 2003 , DOI: 10.1016/s0957-4166(03)00315-x Kenichi Sakai , Rumiko Sakurai , Atsushi Yuzawa , Yuka Kobayashi , Kazuhiko Saigo
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.
中文翻译:
用(S)-扁桃酸拆分3-(甲基氨基)-1-(2-噻吩基)丙-1-醇(度洛西汀的新关键中间体)
研究了外消旋3-(甲基氨基)-1-(2-噻吩基)丙烷-1-醇3(度洛西汀1的新关键中间体)的拆分。条件进行了用于工业规模的分辨率优化3通过使用(小号) -扁桃酸4作为拆分试剂和含有2倍摩尔量的水作为溶剂的2-丁醇。胺释放后,将(S)-3 ·(S)-4 ·H 2 O非对映异构体盐结晶,得到具有> 99.9%ee的纯(S)-3。释放的(-)- 3的绝对构型确定为(S)通过X射线晶体学。
更新日期:2017-01-31
中文翻译:
![](https://scdn.x-mol.com/jcss/images/paperTranslation.png)
用(S)-扁桃酸拆分3-(甲基氨基)-1-(2-噻吩基)丙-1-醇(度洛西汀的新关键中间体)
研究了外消旋3-(甲基氨基)-1-(2-噻吩基)丙烷-1-醇3(度洛西汀1的新关键中间体)的拆分。条件进行了用于工业规模的分辨率优化3通过使用(小号) -扁桃酸4作为拆分试剂和含有2倍摩尔量的水作为溶剂的2-丁醇。胺释放后,将(S)-3 ·(S)-4 ·H 2 O非对映异构体盐结晶,得到具有> 99.9%ee的纯(S)-3。释放的(-)- 3的绝对构型确定为(S)通过X射线晶体学。