Collect. Czech. Chem. Commun. 1987, 52, 2735-2743

Preparation of 21-methoxycarbonyl-21-methylene-5-pregnen-3β-ol derivatives

Vladimír Pouzara, Lenka Kárászováb and Miroslav Havela

a Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6
b Department of Organic Chemistry, Charles University, 128 40 Prague 2


Reaction of 3β-methoxymethoxy-21-nor-5-pregnen-20-ol p-toluenesulfonate (II) with sodium dimethyl malonate afforded dimethyl 3β-methoxymethoxy-5-pregnene-21,21-dicarboxylate (III). Partial hydrolysis of III, followed by reaction with formaldehyde and diethylamine, gave methyl 3β-methoxymethoxy-21-methylene-5-pregnene-21-carboxylate (XVI) which was further transformed into hemisuccinate XIX.