Perchloric Acid → HCID 13477358, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 0.5 g of 17α-acetoxy-6α,16β-dimethyl-4,9(11)-pregnadiene-3,20-dione in 7.7 ml of dioxane and 0.5 ml of water is combined, after adding 380 mg of N-bromosuccinimide, at 20° C. dropwise with a solution of 0.04 ml of 70% strength perchloric acid in 0.6 ml of water. The mixture is agitated for one hour at an internal temperature of 20° C., cooled down to 15° C., and neutralized dropwise with a solution of 1.6 g of sodium acetate and 1.0 g of sodium sulfite in 9.7 ml of water. In this process, the internal temperature must not rise beyond 23° C. After the addition of 5 ml of methanol, the reaction mixture is stirred for 15 minutes at room temperature and, after adding 20 ml of water, for 3 hours at 0° C. Finally, the precipitate is suctioned off, the residue is washed neutral with water and dried at 70° C. in a vacuum-drying cabinet. The crude product is recrystallized from acetone/hexane, thus isolating 380 mg of 17α-acetoxy-9α-bromo-11β-hydroxy-6α,16β-dimethyl-4-pregnene-3,20-dione, mp 162° C. (decomposition).

Provenance & Evidence