Ethylene Oxide → 2-[(3R)-3-methoxymethylmorpholino]ethanol

To a mixed solution of (3R)-3-(methoxymethyl)morpholine hydrochloride (4.71 g) and triethylamine (4.11 ml) in methanol (110 ml) was added 5.8M ethylene oxide (22 ml) in toluene solution at room temperature. After the reaction mixture was stirred at the same temperature for two days, it was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using mixed solvents of dichloromethane and methanol (20:1). The fractions containing the objective compound were collected and evaporated under reduced pressure to give 2-[(3R)-3-methoxymethylmorpholino]ethanol (4.67 g) as an oil.