The United States of America as Represented by the Department of Health

James E Burdett, Jr

Hyun K Kim

Carmie Kirk Acosta

Pemmaraju Narasinha Rao

Methods for the preparation of the 19-norprogesterone of formula I ##STR1## and its intermediates, in crystalline and amorphous forms are disclosed. The process is performed by (1) protecting the hydroxyl group of a compound of formula II ##STR2## (2) reacting the protected compound with an alkali or alkaline earth metal anion radical, (3) hydrolyzing the resulting compound, (4) ketalizing the carbonyl groups, (5) epoxidizing the compound, (6) opening the epoxide ring and introducing an N,N,dimethylamino-phenyl functional group into the axial position of C.sub.11, (7) deketalizing and dehydrating the resulting compound, and (8) acetylating to provide 17.alpha.-acetoxy-11.beta.-(4-N,N-dimethylaminophenyl)-19-norpregna-4,9-di ene-3,20-dione (I).

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Somerset, TX, United States of America

James E Burdett, Jr