[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][NH2:9])[CH:5]=[CH:6][CH:7]=1.O=[C:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[CH2:8][NH:9][CH:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]1To a solution of (3-bromophenyl)methanamine (670 mg, 3.6 mmol), tert-butyl 4-oxopiperidine-1-carboxylate (600 mg, 3 mmol) and sodium triacetoxyborohydride (1.27 g, 6 mmol) in 10 mL of dichloromethane was added acetic acid (360 mg, 6 mmol). The mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure. The residue was purified by column chromatography (silica gel, eluting with petroleum ether:EtOAc=3:1) to give tert-butyl 4-(3-bromobenzylamino)piperidine-1-carboxylate (0.9 g, 68%) as an oil. 1H NMR (300 MHz, CDCl3) δ 7.48-7.47 (m, 1H), 7.38-7.35 (m, 1H), 7.25-7.17 (m, 2H), 4.10 (brs, 1H), 3.79 (s, 2H), 2.85-2.76 (m, 2H), 2.67-2.61 (m, 1H), 1.87-1.82 (m, 2H), 1.45 (s, 9H), 1.37-1.29 (m, 2H).
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