[CH2:1]([O:8][CH2:9][C:10]12[O:16][CH:15]1[CH2:14][N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12][CH2:11]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[NH4+].[OH-].C1COCC1>CCOCC>[CH2:1]([O:8][CH2:9][C:10]1([OH:16])[CH2:15][CH2:14][N:13]([C:17]([O:19][C:20]([CH3:22])([CH3:21])[CH3:23])=[O:18])[CH2:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1An Et2O (25 ml) solution of tert-butyl 6-[(benzyloxy)methyl]-7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate (3.37 g) was added dropwise under ice-cooling to an suspension of LAH (520 mg) in Et2O (75 ml), and was stirred at room temperature for 1 hour, Under ice-cooling, a saturated ammonia aqueous solution (1 ml) was added. After dilution with THF, stirring was performed at room temperature for 2 hours. After drying over anhydrous magnesium sulfate, Celite filtering was performed. The residue obtained by concentration was purified by silica gel column chromatography (EtOAc/hexane) to obtain tert-butyl 4-[(benzyloxy)methyl]-4-hydroxypiperidine-1-carboxylate (2.59 g).
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