METHOD OF PRODUCING 3β-ACETOXY-17α-HYDROPEROXY-16α-METHYLPREGNANES FROM Δ¹⁶-20-KETOSTEROIDS AND METHOD OF PRODUCING 3β-ACETOXY-17α-HYDROXY-16α-METHYLPREGNANES USING 3β-ACETOXY-17α-HYDROPEROXY-16α-METHYLPREGNANES

摘要

FIELD: chemistry.;SUBSTANCE: invention relates to synthesis of organic substances, particularly to synthesis of steroids used in chemical, microbiological and pharmaceutical industries. The invention specifically relates to synthesis of novel 3β-acetoxy-17α-hydroperoxy-16α-methylpregnanes from Δ¹⁶-20-ketosteroids and synthesis of 17α-hydroxy-16α-methylpregnanes using 3β-acetoxy-17α-hydroperoxy-1β-methylpregnanes. 3β-acetoxy-17α-hydroperoxy-1β-methylpregnanes are obtained using a method which involves catalytic 1,4-addition of methyl-magnesium halide to Δ¹⁶-20-ketosteroid in a medium of an aprotic solvent (or mixture of solvents) and subsequent autoxidation of the formed magnesium halide derivative of 3β-acetoxy-20-hydroxy-Δ¹⁷⁽²⁰⁾-16α-methylpregnane with molecular atmospheric oxygen in a heterogeneous medium. 17α-hydroxy-16α-methylpregnanes are produced from 3β-acetoxy-17α-hydroperoxy-16α-methylpregnanes by treating the latter with a reducing agent, where the 17α-hydroxy-16α-methylpregnanes may also be obtained from Δ¹⁶-20-steroids via successive chemical conversions without extraction of 3β-acetoxy-17α-hydroperoxy-16α-methylpregnanes from the solution.;EFFECT: obtaining novel steroids.;20 cl, 8 ex