Water → HCID 86754411, compound

Participants

Reaction Steps

To a solution of (1R)-N1 -(tert-butoxycarbonyl)-1-(1H-indol-3-ylmethyl)-1,2-ethanediamine (1.00 g) in N,N'-dimethylpropyleneurea (10 ml) were added successively ethyl 4-bromobutyrate (0.49 ml) and sodium carbonate (0.73 g) at room temperature in a stream of nitrogen. The mixture was stirred at the same temperature for 45 minutes and then at 110° C. for 3 hours. After cooling to room temperature, water (100 ml) and diethyl ether (50 ml) were added into the mixture. The organic layer was separated and washed with brine, and dried over magnesium sulfate. After evaporation in vacuo, the residue was purified by column chromatography on silica gel (35 g) eluting with a mixture of dichloromethane-methanol (from 0% to 6% gradient solution) to give (1R)-N1 -(tert-butoxycarbonyl)-N2 -[3-(ethoxycarbonyl)-propyl]-1-(1H-indol-3-ylmethyl)-1,2-ethanediamine (0.78 g) as an oil.

Provenance & Evidence