Nitrogen → (17beta)-7-methyl-3-oxo-N-[2-(trifluoromethyl)phenyl]androst-5-ene-17-carboxamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 3.0 M methylmagnesium bromide (2.35 mmol) in ether under a stream of N2 was added 6.0 mL degassed THF. The solution was cooled to 0° C., then CuCl (0.03 g, 0.300 mmol) was added. The mixture was stirred for 5 min. A solution of the compound from Step A (5-2) (0.25 g, 0.55 mmol) in 6.0 mL degassed THF was added. The reaction was warmed to room temperature overnight. It was quenched by slow addition of 2.0 mL degassed water, then diluted with 10% KHSO4 solution and EtOAc. The organic phase was washed with 10% KHSO4 solution, saturated NaHCO3 solution, and brine. After removal of the solvent, the residue was purified by preparative HPLC (C18; 70% MeOH with 5 to 30% MeCN-water) to provide 5-5.

Provenance & Evidence