Hydrochloric Acid → HCID 22884996, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-methyl-6-azaandrost-4-ene-3,16-dione (13, R2 =H) (273 mg, 0.906 mmoles) in THF (15 mL) at 0° C. in a N2 atmosphere was added lithium tri-tertbutoxyaluminum hydride (1.0M/THF) (2.36 mL, 2.6 mmoles) and the mixture stirred at 0° C. for 24 hours. The pH was brought to 4 with 0.5M HCl, and the mixture evaporated in vacuo. The residue was dissolved in methylene chloride and washed with H2O and brine and dried over MgSO4. Evaporation in vacuo and flash chromatography on silica gel with 4% methanol in methylene chloride gave (14, R2 =H) as a white solid. NMR (CDCl3): δ 1.03 (s, 3H, 18-Me); 1.29 (s, 3H, 19-Me); 2.87 (s, 3H, N-CH3); 4.46 (m, 1H, 16-H); 5.32 (s, 1H, 4-H).

Provenance & Evidence