Enantioselective Synthesis of S- and R-Fluoxetine Hydrochloride

Chin. J. Org. Chem. ›› 2006, Vol. 26 ›› Issue (01): 65-68. Previous Articles Next Articles

Original Articles

(S)-和(R)-盐酸氟西汀的不对称合成

程青芳¹,2，许兴友*^,1,2，刘玮炜¹，杨绪杰²，姚泳³

(¹淮海工学院化工系连云港 222005)
(²南京理工大学材料化学实验室南京 210094)
(³江苏正大天晴药业股份有限公司连云港 222006 )

收稿日期:2005-03-24 修回日期:2005-07-18 发布日期:2005-12-31
通讯作者: 许兴友

Enantioselective Synthesis of S- and R-Fluoxetine Hydrochloride

CHENG Qing-Fang¹,2,XU Xing-You*^,1,2,LIU Wei-Wei¹
YANG Xu-Jie²,YAO Yong³

(¹Department of Chemical Technology, Huaihai Institute of Technology, Lianyungang 222005)
(² Materials Chemistry Laboratory, Nanjing University of Science and Technol-ogy, Nanjing 210094)
(³Jiangsu Zhengda Tianqing Pharmaceutical Co., Ltd., Lianyungang 222006)

Received:2005-03-24 Revised:2005-07-18 Published:2005-12-31
Contact: XU Xing-You

Abstract

The enantioselective synthesis of fluoxetine hydrochloride, a potent serotonin-uptake inhibitor, was described. The asymmetric reduction of 3-chloropropiophenone catalyzed by chiral oxazaborolidines enantioselectively gave S- or R-3-chloro-1-phenylpropanol (2) in good yield. In following two steps, alcohol 2 was converted into S- or R-fluoxetine hydrochloride in 66.5% overall yield and 98.6% ee. Some factor effecting the yield and the enantioselectivity of asymmetric reduction of 3-chloropropiophenone was investigated.

Key words: fluoxetine hydrochloride, chiral oxazaborolidine, asymmetric reduction, inhibitor

Cite this article

CHENG Qing-Fang^1,2,XU Xing-You*^,1,2,LIU Wei-Wei
YANG Xu-Jie²,YAO Yong³. Enantioselective Synthesis of S- and R-Fluoxetine Hydrochloride[J]. Chin. J. Org. Chem., 2006, 26(01): 65-68.

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(S)-和(R)-盐酸氟西汀的不对称合成

Enantioselective Synthesis of S- and R-Fluoxetine Hydrochloride

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