Gestonorone

Gestonorone is a steroidal progestin. It has been shown to have accelerated body weight gain and caused the atrophy of the prostate, uterus, and seminal vesicles in rats. It is also an inhibitor of the reductive pathway of Testosterone (T155000) metabolism.

ChEBI: Gestonorone is a corticosteroid hormone.

A solution of (17??)-3-methoxy-17-[(trimethylsilyl)-oxy]-estra-2,5(10)-dien-17-ylmethylnitril in 600 ml of methyl tert-butyl ether was cooled with stirring to -40 ??C, and then 80 ml of N,N,N??,N??-tetramethylethylenediamine and 180 ml of lithium methoxide (3M in diethoxymethane) were added at a rate of less than the -30 ??C temperature. N,N,N??,N??-tetramethylethylenediamine and 180 ml of methyl lithium solution (3M in diethoxymethane), the reaction mixture was stirred at this temperature for 1 h, then poured into 1000 ml of 4N hydrochloric acid solution cooled down to -15 to (-10) ??C by strong cooling, the reaction mixture was stirred at 20-25 ??C for 16 h, and then the pH of the solution was adjusted to 4-5 by adding about 800 ml of 3M sodium acetate. The volatile organic components were removed by distillation and the residue was stirred at 20-25??C for 1 h. The precipitated crude product was filtered, suspended in 5 x 500 ml of water, washed with 100 ml of cold methanol and dried in a vacuum oven. Yield: 32.42 g (67.1%), purity (HPLC): 89.66% . 32.42g of the crude product was added to 97 ml of methanol at 60??C under inert atmosphere and after obtaining a clear solution, the resulting mixture was cooled to 20-25??C. It took 2-3 minutes to add 16.2 ml of water to the stirred slurry, which was then cooled to to 0-5 ??C. After stirring for 1 hour, the crystals were filtered out, suspended in a mixture of 11.2 ml of water and 67.1 ml of methanol, and dried in a vacuum oven. Yield: 25.67 g (79.2%), Purity (HPLC): 98.47%.