[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[O:15][CH:16]=[CH:17][C:18]=2[C:19](OC)=[O:20])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[O:15][CH:16]=[CH:17][C:18]=2[CH2:19][OH:20])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]A solution of 4-(3-methoxycarbonylfuran-2-yl)piperidine-1-carboxylic acid t-butyl ester (550 mg, 1.6 mmol, 1.0 eq.) in THF (15 mL) was added to a solution of LiAlH4 (120 mg, 3.2 mmol, 2.0 eq.) in THF (25 mL) at −30° C. The resulting solution was stirred for 1 hour and allowed to warm to 0° C., then stirred for 1 hour at 0° C. Water (120 mg) was added dropwise to quench the reaction. The mixture was allowed to warn to room temperature, and 15% NaOH (360 mg) and water (120 mg) was added. The mixture was stirred for 1 hour at room temperature. The solids were filtered and the filter cake was washed with EtOAc (20 mL). The residue was applied onto a silica gel column and purified by chromatography with PE/EtOAc (10:1˜5:1). The product was combined with another lot of material, then crystallized (PE/EtOAc=3:1, 1.2 mL), to yield 4-(3-hydroxymethylfuran-2-yl)piperidine-1-carboxylic acid t-butyl ester (0.8 g) as a white solid.
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