Nitrogen → HCID 53819571, compound

Participants

Reaction Steps

To a solution of 6-azaandrost-4-ene-3,16-dione (12, R2 =H) (558 mg, 1.94 mmoles) in DMF (12 mL) was added, in a N2 atmosphere, sodium hydride (60% in mineral oil) (116 mg, 2.91 mmoles) and the mixture stirred at room temperature for 30 minutes. Methyl iodide (1.8 mL, 19.4 mmoles) was added and stirring continued for 2 hours. Saturated NH4Cl (1 mL) was added followed by methylene chloride and H2O. The organic phase was washed with H2O and brine and dried over MgSO4. Evaporation in vacuo and flash chromatography on silica gel with 4% MeOH/CHCl3 gave (13, R2 =H) as a white solid. NMR (CDCl3): δ 0.97 (s, 3H, 18-Me); 1.32 (s, 3H, 19-Me); 2.86 (s, 3H, N-CH3); 5.25 (s, 1H, 4-H).

Provenance & Evidence