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Synthesis of (±), (+), and (−)3β‐(1‐Phenylethylamino)cholest‐5,6‐enes
Author(s) -
Anand Jasbir K.,
Boyce Sam F.
Publication year - 1995
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.19953280606
Subject(s) - diastereomer , chemistry , enantiomer , organic chemistry , stereochemistry
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.