[H-].[Na+].[CH2:3]([O:10][CH2:11][C:12]1([OH:25])[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:26]I.[Cl-].[NH4+]>CCOC(C)=O.CN(C=O)C>[CH2:3]([O:10][CH2:11][C:12]1([O:25][CH3:26])[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:22])([CH3:24])[CH3:23])=[O:19])[CH2:14][CH2:13]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1
55% sodium hydride (4.06 g) was added under ice-cooling to a DMF (100 ml) solution of tert-butyl 4-[(benzyloxy)methyl]-4-hydroxypiperidine-1-carboxylate (9.96 g), and stirring was performed at 50° C. for 40 minutes. Under ice-cooling, methyl iodide (22.0 g) was added dropwise, and the mixture was stirred at room temperature for 4 hours. After adding a saturated ammonium chloride aqueous solution and purified water to the reaction liquid, extraction was performed with EtOAc. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (EtOAc/hexane) to obtain tert-butyl 4-[(benzyloxy)methyl]-4-methoxypiperidine-1-carboxylate (9.27 g).
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