4-Methyltestosterone → (3E,8R,9S,10R,13S,14S,17S)-3-(2-aminoethoxyimino)-4,10,13-trimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-ol;hydrochloride

Beteiligte Stoffe

Reaktionsschritte

To a stirred solution of 4-methyltestosterone (203 mg) in dioxane (3.7 ml), a solution of 2-aminoethoxyamine dihydrochloride (259 mg) in water (2 ml) was rapidly added dropwise. After 24 h dioxane (20 ml) and brine (10 ml) were added and the mixture was stirred for 10 min. The phases were separated and the aqueous phase was extracted with dioxane (2×). The combined organic extracts were washed with brine, dried over MgSO4, filtered and evaporated to dryness. The residue was triturated with Et2O for 5 h and the precipitate was filtered. The crude product was dissolved in water and freeze-dried to give the title compound (I-aa) as a white solid (197 mg, 74%).

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