[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:15]([NH2:19])[CH2:16][CH2:17][CH3:18].C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CN(C)C=O.O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:19][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]To a solution of 1-t-butoxycarbonylpyperidin-4-one (10.0 g) in dimethylformamide (200 mL) were added n-butylamine (6.0 mL) and triethylamine (7.0 mL) and the solution was stirred. To the reaction solution was added sodium triacetoxyborohydride (16.0 g) and the solution was stirred for 1.5 hours. After finishing the reaction, water was added to the reaction solution, which was extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and concentrated to give the title compound having the following physical data.
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