Dehydronorketamine → 6-Biotinoylamino-6-(2-chlorophenyl)-2-cyclohexen-1-one

Participants

Reaction Steps

A solution of 6-amino-6-(2-chlorophenyl)-2-cyclohexen-1-one (50 mg, 0.23 mmol), (+)-biotin (56 mg, 0.23 mmol), hydroxybenzotriazole (31 mg, 0.23 mmol), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (66 mg, 0.35 mmol) in dimethylformamide (1 ml) was stirred at room temperature for 42 h. The reaction was partitioned between water and ethyl acetate, the organic phase was washed with water, brine, dried (Na2SO4), and the solvent removed by evaporation. Flash chromatography on silica gel eluted with 17:3 ethyl acetate/hexane afforded 6-biotinoylamino-6-(2-chlorophenyl)-2-cyclohexen-1-one (32.7 mg, 32%).

Provenance & Evidence