Nitrogen → HCID 53891980, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3β-(hydroxy)androst-5-en-17-one (1, R2 =H) (available from Sigma Chemical Co., St. Louis, Mo., 10.09 g, 35 mmoles, also called dehydroepiandrostenone "DHEA") in methylene chloride (150 mL) in a N2 atmosphere was added lutidine (6.1 mL, 52.5 mmoles) followed by triisopropylsilyl trifluoromethanesulfonate (11.6 mL, 42 mmoles) and the resulting mixture stirred at 0° C. for 25 minutes. The reaction mixture was diluted with methylene chloride (100 mL) and washed with 1N HCl (2 times), H2O, 10% NaHCO3, H2O, brine and dried over MgSO4. Evaporation in vacuo gave 3β-(triisopropylsilyloxy)androst-4-ene-17-one (2, R2 =H) as a white, waxy solid. A mixture of (2) (16.9 g, 35 mmoles), powdered KOH (1.96 g, 35 mmoles) and benzaldehyde (7.83 mL, 77 mmoles) in ethanol (250 mL) was stirred at room temperature in the dark for 18 hours. The mixture was cooled in an ice bath, filtered and the precipitate dried in a vacuum oven at 70° C. for 5 hours to give (3, R2 =H) as a white solid. NMR (CDCl3): δ 1.00 (s, 3H, 18-Me); 1.07 (s, 21H, CH(CH3)2 ; 1.09 (s, 3H, 19-Me); 3.58 (m, 1H, 3-H); 5.38 (d, 1H, 6-H); 7.37-7.57 (m, 6H, =CH--Ph).

Provenance & Evidence