[BH4-].[Li+].[OH:3][CH2:4][CH2:5][CH2:6][C:7]1([C:20](OCC2C=CC=CC=2)=[O:21])[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]1.Cl.C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.C1(C)C=CC=CC=1>[OH:21][CH2:20][C:7]1([CH2:6][CH2:5][CH2:4][OH:3])[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])[CH2:9][CH2:8]1Lithium borohydride (500 mg, 22.7 mmol) was added to a solution of 1-(1,1-dimethylethyl) 4-phenylmethyl 4-(3-hydroxypropyl)-1,4-piperidinedicarboxylate (Description 136, 1.05 g, 2.79 mmol) in tetrahydrofuran/toluene (50:50, 20 mL). and the mixture was stirred at 60° C. for 4 hours. The mixture was cooled and hydrochloric acid (2M, 10 mL) was added. The mixture was poured into aqueous sodium carbonate (10%, 100 mL) and extracted with ethyl acetate (3×50 mL). The combined organic fractions were dried (Na2SO4) and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with EtOAc/MeOH (100:0 increasing to 95:5) to give the title compound (563 mg, 74%). 1H NMR (400 MHz, CDCl3) δ 3.67 (2H, t, J 7 Hz), 3.48 (2H, s), 3.47–3.40 (2H, m), 3.35–3.25 (2H, m), 1.7 (2H, br s), 1.6–1.3 (8H, m), and 1.44 (9H, s).
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