Dimethylformamide → 2-t-Butoxycarbonyl-9-(2-acetoxy-ethyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole

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Reaction Steps

Anhydrous DMF solution (10 ml) of 2-t-butoxycarbonyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole (2.72 g, 10 mol) was mixed with 60% sodium hydride (0.4 g, 10 mmol) and stirred at room temperature for 1 hour. The reaction solution was cooled to −60° C., mixed with 2-acetoxy-1-bromoethane (1.67 g, 10 mmol) and then returned to room temperature while stirring for 1 hour. The reaction solution was mixed with ethyl acetate, 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 mixed with diisopropyl ether (20 ml) and the thus precipitated crystals were collected by filtration to obtain 1.90 g of the title compound (5.3 mmol, 53% in yield).

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