Stereochemical studies. II. Synthesis and deamination of cis-2-Amino-cis-4-t-butyl-1-methylcyclohexanol

Abstract

The title compound (15) has been synthesized unambiguously from 4-t- butyl-1-methylcyclohexene (11). When treated with nitrous acid, it undergoes ?normal? stereospecific deamination to give the ring- contracted product (17) in contrast to the known ?abnormal? behaviour of the related amino sterol (7).