Process for the preparation of 17.beta.-oxalyl steroids

US3960842A · kind A · utility

Assignee

• SCHERING CORPORATION · US

Inventors

• Gregor Haffer · Berlin, DE
• Ulrich Eder · Berlin, DE
• Henry Laurent
• Jurgen Ruppert
• Gerhard Sauer · Berlin, DE
• Rudolf Wiechert · Berlin, DE

Key dates

• Filing date: Jul 12, 1974
• Grant date: Jun 1, 1976
• Expiry date: Jul 12, 1994

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07J21/006
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

20-Cyano-17.alpha.-H steroids having as the 17-position substituent the group ##EQU1## wherein R is H, alkyl of 1-8 carbon atoms or benzyl, having a 13-methyl or 13-ethyl group and which are unsubstituted or substituted with an .alpha.-methyl group in the 16-position are converted to the corresponding 20-keto steroids by reaction in an aprotic solvent with a deprotonating agent containing an alkali metal, an alkaline earth metal, copper(I) or thallium(I), and optionally additionally with a copper(I) salt or a thallium(I) salt or a silver(I) salt, and thereafter conducting an oxidative splitting reaction with oxygen. The thus-produced 17.beta.-oxalyl steroids possess pharmacological activity, e.g., anti-inflammatory activity, or are useful as intermediates for the production of pharmacologically active steroids.