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 5.8 M ethylene oxide (22 ml) in toluene solution at room temperature. After stirring the reaction mixture at the same temperature for 2 days, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography using a mixed solvent of dichloromethane and methanol (20:1). Fractions containing the desired compound were collected and the solvent was evaporated under reduced pressure to give 2-[(3R)-3-(methoxymethyl)morpholino]ethanol (4.67 g) in the form of an oily substance.