Hydrogen Peroxide → (20S)-4,5-epoxy-21-hydroxy-20-methylpregnan-3-one benzoate

Participants

Reaction Steps

A solution of (20S)-21-hydroxy-20-methylpregn-4-en-3-one benzoate (8.9 g, 20.5 mmole) in methanol (80 mL) and dichloromethane (80mL) was cooled to 15° C. and treated sequentially with 30% hydrogen peroxide (5.0 mL) and sodium hydroxide (1.09 g) in water (6.7 mL). After 4 hours at room temperature, the product was isolated from the reaction mixture by the same procedure as described in Example 9 to give (20S)- 4,5-epoxy-21-hydroxy-20-methylpregnan-3-one benzoate (1.6 g, 17.3%). IR 1720, 1280 cm-1 ; MS (CI) 451 (95%, M+1), 329 (100%, M+1-PhCOOH); 1H NMR (CDCl3 3) δ 0.76 (3H, s, C18 -Me), 1.13 (d, C22 -Me), 1.16 (s, C19 -Me), 2.98+3.04 (1H, s +s. C4 -H), 4.04 (1H, dd, 1/2 C21 -CH2), 4.32 (1H, dd, 1/2 C21 -CH2), 7.46 (2H, t), 7.57 (1H, t), 8.04 (1H, dd).

Provenance & Evidence