Mitsubishi Chemical Industries Limited

Ryozo Yamaguchi

Tadashi Oohama

Kunihiro Ninomiya

Mamoru Sugano

Susumu Kanno

Hideo Nagoshi

Haruo Imai

19-Norethisterone or 19-norandrost-4-ene-3,17-dione is purified by passing its solution in an aromatic hydrocarbon, an alkyl halide or an ester of acetic acid through a column packed with basic alumina and then crystallizing it.

Process for the purification of steroids

17-Ketals of 3-alkoxyestra-2,5(10)-dien-17-ones are prepared by reacting 17-ketals of 3-alkoxyestra-1,3,5(10)-trien-17-ones with sodium or potassium, liquid ammonia and a tertiary alcohol in the presence of an alicyclic hydrocarbon and/or an aliphatic hydrocarbon, and a solvent selected from the group consisting of tetrahydrofuran, dioxane and tetrahydropyran. Yield and selectivity of this reaction are improved by using the 17-ketal of the 3-alkoxyestra-1,3,5(10)-trien-17-one, sodium or potassium, liquid ammonia and the solvent in such proportions that the 17-ketal of the 3-alkoxyestra-1,3,5(10)-trien-17-one is substantially dissolved in the reaction system and that two liquid phases are formed, the lower phase being colored.

Process for producing 17-acetals of 3-alkoxyestra-2,5 (10)-dien-17-ones

17-Acetals of 3-alkoxyestra-2,5(10)-dien-17-ones are prepared by reacting 17-acetals of 3-alkoxyestra-1,3-5(10)-trien-17-ones with sodium or potassium, liquid ammonia and a tertiary alcohol in the presence of a solvent selected from the group consisting of tetrahydrofuran, dioxane and tetrahydropyran. Yield and selectivity of this reaction are improved by using the 17-acetals of the 3-alkoxyestra-1,3,5(10)-trien-17-ones, sodium or potassium, liquid ammonia and the solvent in such proportions that the 17-acetals of the 3-alkoxyestra-1,3,5(10)-trien-17-ones are substantially dissolved in the reaction system and that two liquid phases are formed, the lower phase being colored.

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Yokohama, Japan

Ryozo Yamaguchi