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Synthesis 2011(8): 1208-1212  
DOI: 10.1055/s-0030-1259963
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Novel Asymmetric Synthesis of cis-(3R,4R)-N-(tert-Butoxycarbonyl)-4-methyl-3-(methylamino)piperidine

Bao-Yu Haoa,c, Jin-Qiang Liu*b, Wei-Han Zhangc, Xin-Zhi Chen*a
a Department of Chemical and Biological Engineering, Zhejiang University, Hangzhou 310027, P. R. of China
Fax: +86(571)87951615; e-Mail: xzchen@zju.edu.cn; e-Mail: liuque.zju@hotmail.com;
b College of Chemistry and Chemical Engineering, Luoyang Normal University, Luoyang 471022, P. R. of China
c Hutchison MediPharma Innovation for Health, Shanghai 201203, P. R. of China
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Publication History

Received 23 January 2011
Publication Date:
22 March 2011 (online)

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Abstract

cis-(3R,4R)-N-(tert-Butoxycarbonyl)-4-methyl-3-(meth­ylamino)piperidine, a key intermediate for the synthesis of CP-690550 (a potent protein kinase inhibitor), is prepared via an asymmetric approach starting from ethyl 1-benzyl-3-oxopiperidine-4-carboxylate hydrochloride in an overall yield of 49%. The mild conditions and high yields obtained during the synthesis suggest a potential industrial application for this route.

Key words

asymmetric synthesis - protecting groups - piperidines - protein kinase inhibitor - deoxygenation

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