Phenol → (2S)-1-(t-butoxycarbonyl)-2-(1-hydroxy-2-phenoxyethyl)-pyrrolidine

Participants

Reaction Steps

To a solution of (2S)-1-(tert-butoxycarbonyl)-2-(1,2-epoxyethyl)pyrrolidine (1.50 g) in methanol (30 ml) were added phenol (1.50 g) and sodium methoxide (380 mg), and the mixture was stirred under reflux for 16 hours. The reaction mixture was concentrated, and the residue was dissolved in ether, washed with 10% citric acid, saturated aqueous sodium bicarbonate, and saturated brine successively, dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography (eluate: hexane-ethyl acetate) to give 1.10 g of the title compound.

Provenance & Evidence