Potassium Hydroxide → Galeterone

Participants

Reaction Steps

The acetate 4 (1.3 g 3.02 mmol) was dissolved in methanol (20 mL) under an inert Ar atmosphere, and the resulting solution treated with 10% methanolic KOH (8 mL). The mixture was stirred at room temperature for 1.5 h, and then concentrated under reduced pressure at approx. 40° C. to a volume of 10 mL. This solution was poured into ice water (300 mL), and the resulting white precipitate was filtered, washed with water and dried. Crystallization from EtOAc/MeOH gave 5 (1.10 g, 94%), mp 189-190° C.; IR(CHCl3) 2934, 2339, 1609, 1490, 1453, 1291, 1040, 837, 808, 705, 663, 608, 578, 550, 517 cm−1; 1H NMR (300 MHz, CDCl3) δ 1.02 (s, 3H, 18-CH3), 1.07 (s, 3H, 19-CH3), 3.55 (m, 1H, 3α-H), 5.41 (br s, 1H, 6-H), 5.99 (s, 1H, 16-H), 7.30 (m, 2H, aromatic-Hs), 7.54 (s, 1H, aromatic-H), 7.80 (s, 1H, aromatic-H), and 7.96 (s, 1H, 21-H). HRMS calcd 411.2407 (C26H32ON2.Na+). found 411.2396.

Provenance & Evidence