Progesterone, acetate

In the course of the production of medroxy-progesterone acetate (IV), a drug with a strong progestogenic effect, the isomer (V) is also formed from (HI). 

METHYL-3-HYDROXY-4-PYRONE see M. O350 6-METHYL-17-a-HYDROXY-A<5-PROGESTERONE ACETATE see TFOOO... 

Van Deijk WA, Blijham GH, Mellink WAM, Meulenberg PMM Influence of aminc luteth-imide on plasma levels of medroj progesterone acetate its ccwelation with serum coitisoL... 

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). 

However, treatment of cortisone 3,20-bissemicarbazone with acetic anhydride and pyridine removes the 20-semicarbazone group preferentially. Selective removal of a protecting group can be also achieved by a selective reaction to give a new intermediate which can be converted into the desired product ketone. Thus progesterone 20-monoenol acetate (42) is prepared from the 3,20-bisenol acetate (40) via selective electrophilic attack of iodine at C-6 followed by reductive dehalogenation of (41). ... 

More recently, permaleic acid has been recommended as a very satisfactory reagent for the Baeyer-Villiger reaction. It reacts almost as fast as trifluoroperoxyacetic acid and does not require buffering. Unfortunately, neither of these two reagents has been used extensively on 20-keto steroids a patent claims the conversion of progesterone to testosterone acetate with trifluoroperoxyacetic acid, but a later communication describes the ready reaction of 3-keto-A" -steroids with this reagent. 

Medroxyprogesterone Acetate Megestrol Acetate Melengestrol Acetate Norethindrone Pregnenolone Acetate Progesterone... 

Preparation of Ba-Methyi-17-Hydroxy progesterone 17-Acetate 1 g of 6a-methyl-17a-hy-droxyprogesterone was dissolved in a mixture of 10 ml of acetic acid and 2 ml of acetic anhydride by heating. After solution was effected the mixture was cooled to 15°C, and 0.3 g of p-toluenesulfonic acid was added. After allowing the mixture to stand for a period of 2 /a hours at room temperature, the pink solution was poured into ice water to give an amorphous solid which was recovered by filtration. 

The precipitate was washed carefully with water and was then dissolved in 10 ml of methanol and 1.5 ml of methylene chloride. The solution was concentrated to 10 ml, diluted with 0.5 ml of 10% sodium hydroxide, boiled for one minute and cooled. The product, which crystallized on cooling, was recrystallized to give flakes of 6a-methyl-17a-hvdroxy-progesterone 17-acetate, having a MP 205° to 209°C, according to U.S. Patent 3,147,290. 

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