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■ New Approach to (3R,4R)-3-Amino-N-benzyloxycarbonyl-4-hydroxy-hexahydro-1H-azepine Using Ring Expansion of Optically Active Piperidine Derivative

Toshiya Morie and Shiro Kato*

*Discovery Research Laboratories, Dainippon Pharmaceutical Co., Ltd., Enoki 33-94, Suita, Osaka 564, Japan

Abstract

New approach to (3R, 4R)-3-amino-N-benzyloxycarbonyl-4-hydroxyhexahydro-1H-azepine (18), which is the intermediate of the natural product balanol (1), is described. A key step in this method is ring expansion of the optically active piperidine derivative (10) to the corresponding hexahydro-1H-azepine (12) with retention of the configuration.