Process for the preparation of 13.beta.-alkyl-4-gonene-3,17-diones

US4024166A · kind A · utility

Assignee

• SCHERING CORPORATION · US

Inventors

• Gerhard Sauer · Berlin, DE
• Ulrich Eder · Berlin, DE
• Gregor Haffer · Berlin, DE
• Gunter Neef · Berlin, DE
• Rudolf Wiechert · Berlin, DE

Key dates

• Filing date: Oct 10, 1975
• Grant date: May 17, 1977
• Expiry date: Oct 10, 1995

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07J1/0059
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Novel process for the preparation of 13.beta.-alkyl-4-gonene-3,17-diones of the formula ##STR1## wherein R.sub.1 is methyl or ethyl, consists of REACTING A 7A.beta.-ALKYL,5,6,7,7A-TETRAHYDROINDANE-1,5-DIONE WITH FORMALDEHYDE AND AN ARYLSULFINIC ACID OR AN ADDUCT OF FORMALDEHYDE AND ARYLSULFINIC ACID TO PRODUCE A TETRAHYDROINDANE DERIVATIVE; PA1 Hydrogenating the tetrahydroindane derivative with hydrogen in the presence of a palladium-, platinum-, or rhodium-containing hydrogenation catalyst to produce a perhydroindane derivative; PA1 Condensing the perhydroindane derivative in the presence of a proton-accepting agent with a 7,7-alkylenedioxy-3-oxooctanoic acid ester; PA1 Treating the product obtained with a strong aqueous base and then heating the product in an inert solvent to produce a 4,5-secosteroid; PA1 Hydrogenating the 4,5-secosteroid in the presence of a palladium-, platinum-, rhodium-, or nickel-containing hydrogenation catalyst; and PA1 Hydrolyzing and cyclizing the hydrogenated 4,5-secosteroid by treatment with a strong acid.