N-Iodosuccinimide → 2alpha-Iodo-1alpha-methylandrost-4-ene-3,17-dione

Participants

Reaction Steps

3.42 g (10 mmol) of 3-acetoxy-1α-methyl-androsta-2,4-dien-17-one (DE-A 3715869) is dissolved in 40 ml of absolute methanol. 2.25 g (10 mmol) of N-iodosuccinimide is added under nitrogen atmosphere and it is stirred for 1 hour at room temperature. The reaction mixture is added with stirring in 70 ml of ice water and the product is extracted with ethyl acetate. The organic phase is washed with 50 ml of water and dried on sodium sulfate. After chromatography of the crude product on silica gel with ethyl acetate/hexane as mobile solvent, 2.36 g (55.4% of theory) of 2α-iodo-1α-methylandrost-4-ene-3,17-dione is obtained as solid.

Provenance & Evidence