The Upjohn Co.

John M Beaton

Merle G Wovcha

Leo A Kominek

Frederick J Antosz

Alfred B Garcia

Joel E Huber

Amphlett Greg Padilla

Max E Breuer

A process which produces bisnoraldehyde-22-enamines in high yield and sufficiently high purity for copper-catalyzed oxygenation by the process of U.S. Pat. No. 3,661,942 has been developed.

Bisnoraldehyde-22-enamine process

Valuable steroid intermediates, 9.alpha.-hydroxyandrost-4-ene-17.beta.-ol-3-one (9.alpha.-OH testosterone), 9.alpha.-hydroxy-3-ketobisnorchol-4-en-22-ol (9.alpha.-OH BN alcohol) and 9.alpha.-hydroxy-3-ketobisnorchol-4-en-22-oic methyl ester (9.alpha.-OH BN acid methyl ester), prepared by microbiological conversion of steroids having 17-alkyl side chains of 8 to 10 carbons.

Process for preparing 9.alpha.-OH BN alcohol

Process for preparing 9.alpha.-OH BN acid methyl ester

Process for preparing 9.alpha.-OH testosterone

Valuable steroid intermediates, 9.alpha.-hydroxyandrost-4-ene-17.beta.-ol-3-one (9.alpha.--OH testosterone), 9.alpha.-hydroxy-3-ketobisnorchol-4-en-22-ol (9.alpha.--OH BN alcohol) and 9.alpha.---hydroxy-3-ketobisnorchol-4-en-22-oic methyl ester (9.alpha.--OH BN acid methyl ester), prepared by microbiological conversion of steroids having 17-alkyl side chains of 8 to 10 carbons.

Composition of matter and process

The present invention discloses a process for the production of androsta-4,9(11)-diene-3,17-dione type compounds from 9.alpha.-hydroxyandrostenedione type compounds by non-aromatic oxygenated strong acid dehydration.

Non-aromatic oxygenated strong acid dehydration of

This invention relates to a process whereby sterols from various sources are prepared for subsequent fermentation by dissolving the sterols in an organic diluent with subsequent removal of the organic diluent producing high substrate concentrations for fermentation.

Growing community of inventors

Portage, MI, United States of America

John M Beaton