Synthesis of (±), (+), and (-) 3β-(1-phenylethylamino)cholest-5,6-enes

Article abstract of DOI:10.1002/ardp.19953280606

Two diastereomeric derivatives of 3β-(1-phenylethylamino)cholest-5,6-enes, viz. R(+) 7b and S(-) 7c have been synthesized by the reaction of racemic 1-phenylethylamine 1a and cholesteryl p-toluenesulfonate 2. The two isomers 7b and 7c separable by crystallization or by chromatography, were obtained in the ratio of 1:1.5 respectively, resulting in 20% diastereomeric excess of product 7c. The authenticity of diastereomers 7b and 7c was established by obtaining them from the reactions of 2 with R(+) 1b and S(-) 1c enantiomers of 1-phenylethylamine. Besides the steroidal amines (±) 7a, (+) 7b, and (-) 7c, optically enriched mixtures of 1,3-diphenyl-1-butanone 4a were also obtained from these reactions.