Hydrochloric Acid → HCID 18377306, compound

Participants

Reaction Conditions

Reaction Steps

A 2 ml portion of THF solution containing 100 mg (0.30 mmol) of 3-benzyloxycarbonyl-2,3,4,4a-tetrahydro-1H-pyrazino[1,2-a]quinoxalin-5(6H)-one was cooled to 0° C., mixed with 59 μl (0.59 mmol) of borane-dimethyl sulfide complex and stirred overnight at room temperature. The reaction solution was mixed with ice water, stirred for 30 minutes and extracted with ethyl acetate. After drying (Na2SO4), the solvent was removed by evaporation under a reduced pressure, and the thus obtained residue was recrystallized from ethyl acetate-hexane to obtain crude crystals. A 97 mg portion of the crude crystals were dissolved in 2 ml of dichloromethane, and the solution was mixed with 125 μl (0.90 mmol) of triethylamine and 64 μl (0.45 mmol) of anhydrous trifluoroacetic acid and stirred overnight at room temperature. The reaction solution was poured into ice water, acidified by adding 1 N hydrochloric acid and then extracted with ethyl acetate. After drying (Na2SO4), the solvent was removed by evaporation under a reduced pressure, and the thus obtained residue was purified by a silica gel chromatography (30 cc; elution by ethyl acetate-hexane=1:5) to obtain 94 mg (74% in yield) of the title compound.

Provenance & Evidence