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Note | Regular issue | Vol 51, No. 10, 1999, pp.2439-2444
Published online, 1st January, 1970
DOI: 10.3987/COM-99-8631
Diastereoselective Synthesis of trans- 4-Arylpiperidine-3-carboxylic Acid Derivatives from 4-Aryl-1,4-dihydropyridine

Kae-Shyang Shih, Chin-Wei Liu, Yu-Jung Hsieh, Shyh-Fong Chen, Hao Ku, Lee Tai Liu,* Ya-Chuan Lin, Hsiang-Ling Huang, and Chia-Lin Jeff Wang

*Deparatment of Medicinal Chemistry, Development Center for Biotechnology, Hsi-Chih Research Park 102, Lane 169, Kang Ning St, Hsi Chih 221, Taipei Hsien, Taiwan, R.O.C.

Abstract

A convenient procedure for the preparation of trans-3,4-disubstituted piperidines from 4-aryl-1,4-dihydropyridine is described. The diastereoselective synthesis of an unnatural amino acid, trans-4-arylpiperidine-3-carboxylic acid, and its derivatives is exemplified. The key steps include the construction of a trans-3,4-disubstituted piperidine moiety in compound (5), N-methyl carbamate of trans-4-aryl-piperidine-3-carboxylic acid, from 4-aryl-1,4-dihydropyridine-3-carboxylic acid methyl ester (2) via hydrogenation, reduction, and hydrolysis. Reduction of acid (5) with lithium aluminum hydride or with sodium borohydride provided the corresponding carbinol (7) or (8).