16a,17a-Epoxyprogesterone

Uses

Definition

Synthesis

2872-76-6

1097-51-4

The general procedure for the synthesis of 16,17-epoxyprogesterone from the compound (CAS: 2872-76-6) was as follows: 0.496 g of compound (III) (1.5 × 10^-3 mol) was dissolved in 30 mL of acetone and the reaction system was cooled to 0 °C. Subsequently, 0.48 mL of conditioned Jones' reagent was slowly added (preparation of Jones' reagent: 2.67 g of CrO3 was dissolved in 2.3 mL of concentrated sulfuric acid and then diluted to 10 mL with water). After stirring the reaction mixture for 1 h at 0 °C, the progress of the reaction was monitored by thin layer chromatography (TLC) until the reaction was completed. Upon completion of the reaction, 0.5 mL of isopropanol was added to the system to quench the reaction, followed by distillation under reduced pressure to remove the acetone. The reaction mixture was extracted three times with 20 mL of ethyl acetate and the organic phases were combined. The organic phase was washed sequentially with saturated sodium bicarbonate solution and saturated brine, and then dried over anhydrous sodium sulfate. The dried organic phase was concentrated under reduced pressure and the resulting residue was purified by column chromatography to afford 0.446 g of white solid 16α,17α-epoxypregn-4-ene-3,20-dione (IV) in 90.6% isolated yield.

References