Collect. Czech. Chem. Commun. 1991, 56, 2884-2891

Synthesis of (19E)-17β-hydroxy-3-oxo-5α-androstan-19-al 19-(O-carboxymethyl)oxime

Jan Fajkoš and Vladimír Pouzar

Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6


The title compound IX was synthesized from triol diester I. Catalytic hydrogenation over Adams’ catalyst afforded the 5α and 5β isomers II and III which were oxidized under mild conditions to the aldehydes IV and XII. Reaction with (O-carboxymethyl)hydroxylamine hemihydrochloride followed by methylation with diazomethane gave the oximes VIII and XIV. Partial hydrolysis to the alcohols VI and XIII and Jones’ oxidation yielded the 3-oxo derivatives XI and XVI. Complete hydrolysis of the diester XI afforded the desired hapten IX.