Bromination of 2-Oxo Steroids

概要

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Bromination or enol acetylation of cholestan-2-one proceeds only towards C-3. Kinetically controlled bromination yields the axial 3α-bromo ketone, which can be equilibrated with hydrogen bromide to a ca. 1 : 1 mixture of 3α- and 3β-bromide. The latter is produced, together with cholest-3-en-2-one, upon treatment of 3α-bromocholestan-2-one with lithium cabonate and lithium bromide in dimethylformamide. 1α-Bromocholestan-2-one, synthesized independently from 1α, 2α-epoxycholestane, is not an intermediate in the formation of the 3α-bromo-2-ketone and is recovered unchanged after exposure to hydrogen bromide. The preparation of 2β-bromocholestan-1-one and its reaction with silver nitrate in acetic acid are also reported as are unsuccessful attempts to form the enol acetate of cholestan-1-one.
公益社団法人日本薬学会の論文
1963-04-25