Synlett 2019; 30(10): 1228-1230
DOI: 10.1055/s-0037-1611553
letter
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Synthesis of cis-(S,R)-3-Amino-4-fluoro-1-methylpyrrolidine

Zhongbo Fei
a   Chemical and Analytical Development, Suzhou Novartis Pharma Technology Co., Ltd, Changshu, Jiangsu 215537, P. R. of China   eMail: jianwei.bian@novartis.com
,
Xin Xiong
a   Chemical and Analytical Development, Suzhou Novartis Pharma Technology Co., Ltd, Changshu, Jiangsu 215537, P. R. of China   eMail: jianwei.bian@novartis.com
,
Chiming Cheung
a   Chemical and Analytical Development, Suzhou Novartis Pharma Technology Co., Ltd, Changshu, Jiangsu 215537, P. R. of China   eMail: jianwei.bian@novartis.com
,
Weipeng Liu
a   Chemical and Analytical Development, Suzhou Novartis Pharma Technology Co., Ltd, Changshu, Jiangsu 215537, P. R. of China   eMail: jianwei.bian@novartis.com
,
Qirong Shen
b   Zhejiang Jiuzhou Pharmaceutical Technology Co., Ltd., Jiangling Road 88, Binjiang, Hangzhou, Zhejiang 310000, P. R. of China
,
Jinzhu Zhang
b   Zhejiang Jiuzhou Pharmaceutical Technology Co., Ltd., Jiangling Road 88, Binjiang, Hangzhou, Zhejiang 310000, P. R. of China
,
Hongjun Gao
b   Zhejiang Jiuzhou Pharmaceutical Technology Co., Ltd., Jiangling Road 88, Binjiang, Hangzhou, Zhejiang 310000, P. R. of China
,
Jianwei Bian*
a   Chemical and Analytical Development, Suzhou Novartis Pharma Technology Co., Ltd, Changshu, Jiangsu 215537, P. R. of China   eMail: jianwei.bian@novartis.com
› Institutsangaben

All work described in this paper was funded by Novartis, Inc.
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Publikationsverlauf

Received: 14. März 2019

Accepted after revision: 30. April 2019

Publikationsdatum:
20. Mai 2019 (online)


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Abstract

The development of the stereoselective synthesis of cis-(S,R)-3-amino-4-fluoro-1-methylpyrrolidine is described starting from chiral, non-racemic 1-[(3S,4S)-3-azido-4-hydroxypyrrolidin-1-yl]-2,2,2-trifluoroethan-1-one. Two sets of deoxyfluorination conditions are developed for achieving inversion of the chiral center with high or complete stereoselectivity.

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