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Report | Regular issue | Vol 22, No. 6, 1984, pp.1411-1415
Published online, 1st January, 1970
DOI: 10.3987/R-1984-06-1411
A Stereoselective Synthesis of 1,5-Disubstituted Thieno[3’,2’:3,4]piperidino[1,2-c]oxazolidin-3-ones through N-Oxaacyliminium Ion Cyclization

Shinzo Kano,* Yoko Yuasa, Tsutomu Yokomatsu, and Shiroshi Shibuya

*School of Pharmacy, Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan

Abstract

A stereoselective synthesis of 1-phenyl- (5) and 5-methyl-1-phenylthieno[3’,2’:3,4]piperidino[1,2-c]oxazolidin-3-ones (8a,b) was achieved by reduction of the corresponding N-substituted 5-phenyloxazolidine-2,4-diones (4, 7a,b) with diisobutylaluminum hydride, followed by treatment of the reduction products with formic acid. Reduction of 8a,b with LiAlH4 afforded the corresponding 4-(α-hydroxybenzyl)-6-methylthieno[3,2-c]pyridines (10a,b), respectively.