The Upjohn Co.

Kenneth P Shephard

Verlan H Van Rheenen

Two processes are disclosed (one-pot and two-pot) for the transformation of a 6.beta.-fluoro-.DELTA..sup.1,4 -3-keto steroid (IV) to a 6.alpha.-fluoro-.DELTA..sup.1,4 -3-keto steroid (VI). These processes permit the introduction of a fluorine atom at the 6.alpha. position of a .DELTA..sup.1,4 -3-keto steroid where previously the .DELTA..sup.1 double bond could not be introduced until after the 6.alpha.-fluorine atom was present. The 6.alpha.-fluoro-.DELTA..sup.1,4 -3-keto steroids (VI) are intermediates useful in the production of pharmacologically active steroids.

Process for producing 6.alpha.-fluoro-.DELTA..sup.1,4 -3-keto steroids

11.beta.,21-Dihydroxypregna-1,4,17(20)-triene-3-one 21-acetate (0) is epoxidized, followed by ring opening and hydrolysis to give 11.beta.,20,21-trihydroxypregna-1,4,16-triene-3-one 21-acetate (III), an intermediate in the synthesis of betamethasone, in improved yields.

Epoxide 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 forming a sulfinate ester at C.sub.9 followed by desulfination.

Desulfinylation process for preparing androsta-4,9(11)-diene-3,17-dione

This invention discloses a general process for the production of corticoids from androstenes. This invention provides an economically viable alternative synthesis of 17.alpha.-hydroxyprogesterones and the corticoids.

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Portage, MI, United States of America

Kenneth P Shephard