9,10-Secoestrane derivatives and their production

US3998847A · 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: Apr 21, 1975
• Grant date: Dec 21, 1976
• Expiry date: Apr 21, 1995

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07C69/01
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

9,10-Secoestranes, useful as intermediates in the total synthesis of steroids, of the formula ##STR1## wherein n is 1 or 2, R.sub.1 is lower alkyl, R.sub.2, R.sub.3 and R.sub.4 are hydrogen, alkoxy or acyloxy, X is free or ketalized carbonyl or free, esterified or etherified hydroxymethylene, and Y is carbonyl or dialkoxymethylene are produced by condensing, in the presence of a basic catalyst, ##STR2## WHEREIN X, n, R.sub.1, R.sub.2, R.sub.3, R.sub.4 have the values given above, and Z is Cl, Br or I, to produce a 9,10-secoestrane of the above formula wherein Y is a free carbonyl group, which can then, if desired, be ketalized to a corresponding compound wherein Y is dialkoxymethylene or like ketal group.