Process for the synthesis of the hydroxyacetyl side-chain of...

Details Process for the synthesis of the hydroxyacetyl side-chain of... Process for the synthesis of the hydroxyacetyl side-chain of...

C - Chemistry, Metallurgy

07

J

260/28, 260/4

C07J 5/00 (2006.01) C07J 1/00 (2006.01) C07J 31/00 (2006.01) C07J 33/00 (2006.01) C07J 41/00 (2006.01) C07J 63/00 (2006.01)

Patent

CA 1140538

Abstract of the Disclosure The present invention relates to a novel general process for synthesising a .alpha.- or .beta.-oriented hydroxy- acetyl side chain of steroids of the pregnane type, which comprises treating a corresponding steroid carbaldehyde in succession with formaldehyde dimethylmecaptal-S-oxide in the form of an alkali metal salt thereof, and with a strongly acid hydrolysing agent. Preferred final products are compounds of the formula Image (IA) wherein n is 1 or 2, R2 represents methyl or difluoro- methyl, and R1 represents hydroxymethyl, methoxymethyl, acetoxymethyl or hydrogen, and, if n is 2 and/or R2 is difluorometyl, R1 also represents methyl. These compounds act as agonists or antagonists of natural steroid hormones. The antigestagenic 19,21-dehydroxy-17.alpha.-pregn-4-ene-3,20- dione and its 6,7-dehydro derivatives and diacetates are of particular interest.

328276

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