Ethyl bromoacetate → 4-(1-tert-Butoxycarbonylpyrrolidin-3-yloxy)phenoxyacetic acid ethyl ester

Participants

Reaction Steps

To a solution of 4-(1-tert-butoxycarbonylpyrrolidin-3-yloxy)phenol (2.14 g) in tetrahydrofuran (43 l) were added ethyl bromoacetate (1.1 ml) and 60% sodium hydride (368 mg) with ice-cooling, and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, ice water was added and the mixture was extracted with ethyl acetate and washed with 10% aqueous citric acid solution. The organic layer was dried over anhydrous magnesium sulfate and the solvent was evaporated. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=7:3) and dried under reduced pressure to give the title compound (2.605 g).

Provenance & Evidence