Benzyl Alcohol → 2-(Benzyloxycarbonylaminomethyl)indan

Participants

Reaction Steps

Dissolved in 150 ml of toluene were 17.6 g (0.10 mol) of 2-(indan-2-yl)acetic acid, and 15.3 ml (0.11 mol) of triethyl-amine and 33.0 g (0.12 mol) of diphenylphosphoryl azide were added to the solution. After the mixture was stirred at room temperature for 30 minutes, 16.6 g (0.15 mol) of benzyl alcohol were added, and the resultant mixture was refluxed for 18 hours. After cooling the mixture, the solvent was distilled off under reduced pressure, and the residue was dissolved in 500 ml of ethyl acetate, washed with 1N sodium hydroxide and then concentrated. The resultant residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:3), and the resultant crystal was recrystallized from a mixed solvent of ethyl acetate and hexane to obtain 24.3 g of 2-(benzyloxycarbonylamino-methyl)indane as a colorless needle crystal. Yield: 86%.

Provenance & Evidence