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

Author

Bao-Yu Hao, Jin-Qiang Liu, Wei-Han Zhang, and Xin-Zhi Chen

Subjects
chemistry.chemical_compound, Chemistry, Stereochemistry, medicine.drug_class, Yield (chemistry), Organic Chemistry, Enantioselective synthesis, medicine, Piperidine, Protein kinase inhibitor, Deoxygenation, Catalysis
Abstract

CIS-(3 R,4 R)- N-( TERT-Butoxycarbonyl)-4-methyl-3-(meth-ylamino)piperidine,a key intermediate for the synthesis of CP-690550 (a potent proteinkinase inhibitor), is prepared via an asymmetric approach startingfrom ethyl 1-benzyl-3-oxopiperidine-4-carboxylate hydrochloridein an overall yield of 49%. The mild conditions and highyields obtained during the synthesis suggest a potential industrialapplication for this route.

Published
2011
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