Dimethylformamide → 2-t-Butoxycarbonyl-9-allyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole

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Reaction Conditions

Reaction Steps

Anhydrous DMF solution (10 ml) of 2-t-butoxycarbonyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole (4.40 g, 16.2 mmol) was mixed with 60% sodium hydride (700 mg, 10 mmol) and stirred at roam temperature for 1 hour. The reaction solution was cooled to −60° C., mixed with allyl bromide (2.18 g, 18 mmol) and then returned to room temperature by further stirring for 1 hour. The reaction solution was mixed with ethyl acetate (150 ml), washed with water and dried with anhydrous sodium sulfate, and then the solvent was removed by evaporation under a reduced pressure. The thus obtained residue was purified by a silica gel chromatography to obtain 4.32 g of the title compound as an oil (13.8 mmol, 87% in yield).

Provenance & Evidence