Azobisisobutyronitrile → HCID 86589971, compound

Participants

Reaction Steps

To 1α,3β-bis(tert-butyldimethylsilyloxy)-17β-(N,N-dimethylaminocarbonylethoxymethyl)androst-5-ene (15 g), were added N-bromosuccinimide (5.36 g), 2,2′-azobis isobutyronitrile (1.06 g), hexane (120 ml) and tetrahydrofuran (30 ml), followed by reflux under heating for 15 min. After cooling to room temperature, the mixture was filtered to remove insoluble material and the filtrate was concentrated under reduced pressure. To the resultant, were added toluene (50 ml) and γ-collidine (9.8 ml), followed by reaction under reflux for 2 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was washed with 0.5M hydrochloric acid, a saturated aqueous sodium bicarbonate solution and then saturated brine. The organic layer was dried over anhydrous magnesium sulfate, concentrated under reduced pressure. To the thus obtained residue, were added dichloromethane (70 ml) and 4-phenyl-1,2,4-triazoline-3,5-dione, followed by reaction at room temperature. The reaction mixture was washed with water, dried over anhydrous magnesium sulfate and evaporated under reduced pressure to remove the solvent. The thus obtained residue was purified by column chromatography (hexane:ethyl acetate=1:2) to give the titled compound (7.43 g).

Provenance & Evidence