Cl.[CH3:2][O:3][CH2:4][C@@H:5]1[CH2:10][O:9][CH2:8][CH2:7][NH:6]1.C(N(CC)CC)C.[CH2:18]1[O:20][CH2:19]1>CO.C1(C)C=CC=CC=1>[CH3:2][O:3][CH2:4][C@H:5]1[N:6]([CH2:18][CH2:19][OH:20])[CH2:7][CH2:8][O:9][CH2:10]1To 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.
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