Sodium Hydroxide → HCID 15007453, compound

Participants

Reaction Steps

The compound, 3-chloroestra-1,3,5(10)-trien-17-one (2.17 g) is added to a solution of 3-(trifluoromethyl)benzylamine (2.6 g) in methanol (200 ml) and tetrahydrofuran (200 ml) made acidic with acetic acid (1.5 ml). When the starting material is dissolved, sodium cyanoborohydride (0.72 g) is added, the mixture is stirred 24 hours, additional sodium cyanoborohydride (0.7 g) is and the mixture is stirred for another 21 hours. The mixture is diluted with water (200 ml), made basic with 50% sodium hydroxide and extracted with methylene chloride (3×100 ml). The combined extracts are washed with brine, dried over magnesium sulfate and the solvent is removed. The product is chromatographed on silica gel and recrystallized in methylene chloride/hexane to give the title compound (2.26 g).

Provenance & Evidence