[OH:1][C@:2]1(CO)[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[O:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:3]1.ClC1C=C(N(C2C=CC=CC=2)C(Cl)=O)C=CC=1.Cl>N1C=CC=CC=1>[CH2:17]([O:16][C:14]([CH2:13][O:12][C:8]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:9]=1[CH2:10][CH2:11][CH:2]([OH:1])[CH2:3]2)=[O:15])[CH3:18]A mixture of (2R)-2-hydroxy-2-(hydroxymethyl)-5-[(ethoxy carbonyl)methoxy]-1,2,3,4-tetrahydronaphthalene (465 mg) and N-(3-chlorophenyl)-N-phenylcarbamoyl chloride (2.21 g) in pyridine (10 mL) was stirred at 100° C. for 24 hours. After cooling, the reaction mixture was poured into 3N hydrochloric acid (50 mL) under ice-cooling and extracted with EtOAc The organic layer was washed with water, saturated sodium hydrogen carbonate, water, and brine, dried over magnesium sulfate, evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane-EtOAc 3:2) to give (2R)-2-{N-(3-chlorophenyl)-N-phenylcarbamoyloxy]methyl}-5-[(ethoxycarbonyl)methoxy]-2-hydroxy-1,2,3,4-tetrahydronaphthalene (800.6 mg) as a solid.
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