N,N-Dimethylacrylamide → HCID 69630616, compound

Participants

Reaction Steps

To 1α,3-bis(tert-butyldimethylsilyloxy)-17β-(hydroxymethyl)androst-5-ene (18.4 g), was added N,N-dimethylacrylamide (9.95 g), sodium hydride (60% in oil, 2.0 g), 15-crown-5 (2.2 g) and tetrahydrofuran (73.5 ml), followed by reaction at 0° C. for 8 hours. After stopping the reaction by adding a saturated aqueous ammonium chloride solution, the organic layer was washed with a saturated aqueous sodium bicarbonate solution and saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure to remove the solvent. The resulting residue was mixed with methanol (90 ml), stirred at room temperature while under suspension, followed by centrifugation. The thus obtained solid was dried to give the titled compound (13.2 g).

Provenance & Evidence