Schering Aktiengesellschaft

Hanfried Arnold

Klaus Nickisch

Jean-Claude Hilscher

Reinhold Wieske

1-Methylandrosta-1,4-diene-3,17-dione is prepared by a process wherein a 3-enol ester or 3-enol ether of general Formula II ##STR1## wherein R.sub.1 is an alkyl residue of 1-3 carbon atoms or an acyl or trialkylsilyl group of up to 10 carbon atoms in the group, is converted into the 2-bromo steroid of Formular III ##STR2## wherein the bromine substituent can be in the .alpha.- as well as in the .beta.-position, and the compound of general Formula III is converted into 1-methylandrosta-1,4-diene-3,17-dione.

Process for the preparation of 1-methylandrosta-1,4-diene-3,17,dione,

A multistep process for production of 17.alpha.-acetoxy-1,2-methylene-4,6-pregnadiene-3,20-dione involves ketalization of the 20-keto group of 17.alpha.-hydroxy-1,4,6-pregnatriene-3,20-dione, then methylenation in the 1,2-position with trimethylsulfoxonium iodide, hydrolysis and simultaneous acetylation of the 17.alpha.-hydroxy group.

Process for the production of

Alkali metal salts of estrogen hemisulfates are stabilized with sodium acetate.

Stabilizer for estrogens

3-Hemisulfate sodium salts of 17.alpha.-hydroxy steroids of the formula ##STR1## wherein R.sub.1 is H, CH.sub.3 or C.sub.2 H.sub.5 and .DELTA. is one or more additional double bonds optionally present in the B and/or C rings are produced by treating a 17-mono ester of a carboxylic acid of up to 15 carbon atoms of the corresponding 3,17.alpha.-dihydroxy steroid with the reaction product of pyridine or like amine and sulfur trioxide or reactive functional derivative thereof and, without isolation thereof, saponifying the resultant reaction product with alkali, preferably a sodium alcoholate or hydroxide in a lower alcohol.

Growing community of inventors

Berlin, Germany

Hanfried Arnold