6,9-Oxido-9,10-secoestrane derivatives and method of synthesis

US3965124A · kind A · utility

Assignee

• SCHERING CORPORATION · US

Inventors

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

Key dates

• Filing date: Jun 18, 1975
• Grant date: Jun 22, 1976
• Expiry date: Jun 18, 1995

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07J51/00
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

6,9-Oxido-9,10-seco-1,3,5(10),6,8,14-estrahexaenes, useful as intermediates in the total synthesis of steroids, of the formula ##SPC1## Wherein n is 1 or 2, R.sub.1 is lower-alkyl, R.sub.2, R.sub.3 and R.sub.4 are H, alkoxy or acyloxy, X is a free or ketalized keto or free, esterified or etherified hydroxymethylene, are produced by the cyclization, with an acid catalyst, of a 9,10-secoestrane of the formula ##SPC2## Wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, X and n have the values given above and Q is carbonyl or dialkoxymethylene. Hydrogenation produces the corresponding 6,9-oxido-9,10-seco-1,3,5(10)-estratrienes and 9-oxy-9,10-seco-1,3,5(10)-estratrienes.