Bicycloalkanes

US4008253A · kind A · utility

Assignee

• SCHERING CORPORATION · US

Inventors

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

Key dates

• Filing date: Dec 22, 1972
• Grant date: Feb 15, 1977
• Expiry date: Dec 22, 1992

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D319/06
• 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 free or ketalized carbonyl or a free, esterified, 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 alkyl, aryl, or aralkyl, R.sub.3 is hydrogen or lower alkyl, R.sub.4 is alkoxycarbonyl, or acyl or phenyl optionally substituted with lower alkoxy or benzyloxy- or acyloxy; and Z is nitrile, nitro, lower alkoxycarbonyl, 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.