Pyridine → Osaterone acetate

Participants

Reaction Steps

A mixture of 70 mg of 17α-acetoxy-6β-chloro-7α-hydroxy-2-oxa-4-pregnene-3,20-dione, 400 mg of p-toluenesulfonyl chloride, 1 ml of 4-dimethylaminopyridine and 0.9 ml of pyridine was heated under reflux for 2 hours. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with 50% hydrochloric acid and then with a saturated aqueous solution of sodium hydrogen carbonate, and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the crude product was purified by TLC [developing solvent: chloroform/acetone (19/1)] to give 52 mg of 17α-acetoxy-6-chloro-2-oxapregna-4,6-diene-3,20-dione. The 1H-NMR spectrum of this compound was the same as that of the compound produced in Example 1.

Provenance & Evidence