Novel bicycloalkane derivatives and the production thereof

US4051188A · kind A · utility

Assignee

• SCHERING CORPORATION · US

Inventors

• Gerhard Sauer · Berlin, DE
• Helmut Hauser · Unna, DE
• Gregor Haffer · Berlin, DE
• Juergen Ruppert · Berlin, DE
• Ulrich Eder · Berlin, DE
• Rudolf Wiechert · Berlin, DE

Key dates

• Filing date: Dec 27, 1976
• Grant date: Sep 27, 1977
• Expiry date: Dec 27, 1996

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D317/46
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Bicycloalkane derivatives of the formula ##STR1## WHEREIN N IS 1 OR 2, R.sub.1 is lower alkyl, X is carbonyl or a free or etherified hydroxymethylene, and Y is --S--R.sub.2, --SO.sub.m --R.sub.2, or ##STR2## wherein m is 1 or 2, R.sub.2 is aryl or aralkyl, R.sub.3 is hydrogen or lower alkyl, R.sub.4 is phenyl optionally substituted with lower alkoxy or benzyloxy, and Z is nitro, lower alkanoyl, lower alkylsulfinyl, or lower alkylsulfonyl, are useful intermediates in the total synthesis of steroids. The compounds are prepared by reacting a corresponding compound lacking the CH.sub.2 Y substituent with formaldehyde and a mercaptan or a sulfinic acid, followed if desired by oxidation and optional salt condensation.