Acetic Anhydride → HCID 10861689, compound

Participants

Reaction Steps

To a mechanically stirred solution of 17β-carbomethoxy-3β-hydroxy-5-androstene (100 g, 0.30 mol), prepared as described in Rasmusson et al., Journal of Medicinal Chemistry 1984, 27, 1690, incorporated herein by reference, in pyridine (750 mL) in a 2 L 4-necked round bottom flask equipped with an addition funnel at ambient temperature is added acetic anhydride (130 mL, 1.38 mol). The resulting dark solution is stirred at ambient temperature for 18 h, transferred to an addition funnel, and added drop wise to 3 L of ice-water. The resulting precipitate is collected by filtration, washed with 2×1 L H2O, and dried under vacuum to afford 17β-carbomethoxy-3β-acetoxy-5-androstene; 1H NMR (400 MHz, CDCl3) δ5.36 (br d, J=5.1 Hz, 1H), 4.59 (m, 1H), 3.67 (s, 3H), 2.37-2.29 (m, 3H), 2.20-2.08 (m, 1H), 2.03 (s, 3H), 2.02-1.97 (m, 2H), 1.90-1.38 (m, 10H), 1.34-1.21 (m, 2H), 1.18-1.05 m, 2H), 1.02 (s, 3H), 1.00-0.96 (m, 1H), 0.66 (s, 3H).

Provenance & Evidence