Diisobutylaluminumhydride → HCID 66705597, compound

Participants

Reaction Conditions

Reaction Steps

Diisobutylaluminum hydride (1 M in methylene chloride) (31 mL, 31 mmol) was added to a −78° C. solution of 2-[(4-bromophenyl)acetyl]-4-(2,2-dimethylbutyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide (intermediate 8) (7.03 g, 15.5 mmol) in methylene chloride (100 mL). After stirring at −78° C. for 1 h, the reaction mixture was quenched with saturated aqueous sodium potassium tartrate and stirred vigorously at ambient temperature until layers separated. The aqueous phase was extracted with methylene chloride. The combined organic extracts were dried (magnesium sulfate) and concentrated in vacuo. Chromatography over silica eluting with 0-100% ethyl acetate/hexane afforded 2-[2-(4-bromophenyl)-1-hydroxyethyl]-4-(2,2-dimethylbutyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide.

Provenance & Evidence