HCID 68973002, compound → HCID 68973350, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3.0 M MeMgBr (0.36 mL, 1.09 mmol) in ether under N2 was added 2.2 mL Argon-purged, anhydrous THF. The mixture was cooled to 0° C. CuCl (0.014 g, 0.14 mmol) was added, and the reaction was stirred for 5 min before adding (17β)-6-methylene-3-oxo-N-[4-(trifluoromethyl)phenyl]androst-4-ene-17-carboxamide (3-4) (0.12 g, 0.25 mmol) as a solid. After several hours the reaction was quenched by dropwise addition of 5.0 mL of Ar-purged water, then partitioned between CHCl3 and 10% KHSO4 solution. The organic phase was washed with saturated NaHCO3 solution and brine, then dried with MgSO4 and concentrated. The residue was purified by flash silica gel chromatography (0 to 30% EtOAc/hexane) and concentrated to yield a clear, colorless oil, which was further purified by preparative HPLC (C18; 70% MeOH with 5 to 30% MeCN-water) to provide the desired product.

Provenance & Evidence