Steroids and Walden inversion. Part LVIII. The Deamination of 3β- and 3α-amino-5α-cholestane

Abstract

Deamination of 3β-amino-5α-cholestane (NH₂, eq) in aqueous acetic acid and analysis of the products by gas chromatography does not confirm the earlier claim for complete retention of configuration unaccompanied by elimination. The results disclose predominant but not exclusive retention accompanied by some elimination. Deamination of 3α-amino-5α-cholestane (NH₂, ax) in aqueous acetic acid effectively substantiates the claim for complete retention of configuration accompanied by much elimination. It seems probable by analogy that these stereochemical patterns also apply to deamination of other equatorial and axial steroid amines.