General procedure for the synthesis of (R)-N-(2,3-epoxypropyl)phthalimide from 3-hydroxy-1H-isoindol-1-one and (R)-epoxyethylene-2-methanol: To a solution of tetrahydrofuran (THF, 220 mL) containing phthalimide (6.6 g, 45.0 mmol), triphenylphosphine (PPh3, 17.7 g, 67.5 mmol), diethyl azodicarboxylate (DEAD, 11.7 mL, 67.5 mmol), and (R)-(+)-condensate were sequentially added. 67.5 mmol), diethyl azodicarboxylate (DEAD, 11.7 mL, 67.5 mmol) and (R)-(+)-glycidol (4.0 g, 54.0 mmol). The reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, the THF solvent was removed by distillation under reduced pressure and the residue was purified by silica gel fast column chromatography (Biotage system, eluent: 5%-20% ethyl acetate/hexane) to afford the target product (R)-N-(2,3-epoxypropyl)phthalimide (5.8 g, 75% yield).
