Medroxyprogesterone

Medroxyprogesterone acetate (74) is stmcturaHy related to and has been prepared from hydroxyprogesterone (39) (Fig. 10). Formation of the bis-ketal accomplishes the protection of the ketones and the required migration of the double bond. Epoxidation with peracetic acid produces a mixture of epoxides (75), with a predominating. Treatment of the a-epoxide with methyl magnesium bromide results in diaxial opening of the epoxide. Deprotection of the ketones provides (76), which is dehydrated to (77) by treatment with dilute sodium hydroxide in pyridine. Upon treatment with gaseous hydrochloric... [Pg.216]

Fig. 10. Preparation of medroxyprogesterone acetate (74) and medroxyprogesterone (78) from hydroxyprogesterone (39).

Megestrol acetate (79) is stmcturaHy related to progesterone (1). It has been prepared from medroxyprogesterone acetate (74) by chloranil-mediated dehydrogenation. It also has been prepared from hydroxyprogesterone acetate (42) via 6-methylenation and double-bond migration (109,110). [Pg.217]

The pregnanes include megestrol, medroxyprogesterone acetate [71-58-9] C24H34O4 (6), chlormadinone acetate [302-22-7] C23H2QCIO4, and cyproterone acetate [427-51-0], C24H2gC104 (7). [Pg.116]

Medroxyprogesterone Acetate Megestrol Acetate Melengestrol Acetate Norethindrone Pregnenolone Acetate Progesterone... [Pg.445]

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