[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([N+:19]([O-])=O)=[C:7]([N:9]2[CH2:14][CH2:13][CH:12]([C:15]([O:17][CH3:18])=[O:16])[CH2:11][CH2:10]2)[CH:8]=1)=[O:2].[H][H]>[Pd].CCOC(C)=O>[NH2:19][C:6]1[CH:5]=[CH:4][C:3]([CH:1]=[O:2])=[CH:8][C:7]=1[N:9]1[CH2:14][CH2:13][CH:12]([C:15]([O:17][CH3:18])=[O:16])[CH2:11][CH2:10]1To methyl 1-(5-formyl-2-nitrophenyl)piperidine-4-carboxylate 64 (0.881 g, 3.0 mmol) was added EtOAc (20 mL) and palladium (0.482 mg, 0.45 mmol). The nitrogen atmosphere was replaced by hydrogen from a double balloon and the reaction mixture was stirred at room temperature for 3 h, filtered, and concentrated in vacuo. Purification by flash column chromatography on silica gel (eluted with 50% to 100% EtOAc in hexanes) gave methyl 1-(2-amino-5-formylphenyl)piperidine-4-carboxylate 65 (0.043 g, 5.4% yield) as a yellow oil. Mass spectrum: calculated for C14H18N2O3 262.1. found 263.2 (M++1). In addition, methyl 1-(2-amino-5-(hydroxymethyl)phenyl)piperidine-4-carboxylate 66 (0.534 g, 67% yield) was isolated as a yellow solid. Mass spectrum: calculated for C14H20N2O3 264.2. found 265.2 (M++1).
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