[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH:10]([N+:20]([O-])=O)[CH2:11][CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:6]=[CH:7][CH:8]=1.C([O-])=O.[NH4+]>[Pd].CO>[NH2:20][CH:10]([CH2:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)[CH2:11][CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14]A mixture of tert-butyl 5-(3-methoxyphenyl)-4-nitrovalerate (0.31 g), 10% palladium on carbon (0.31 g), and ammonium formate (0.63 g) in methanol (3.1 ml) was stirred at ambient temperature for 0.5 hour. After the insoluble material was removed by filtration, the filtrate was evaporated in vacuo. To the residue, ethyl acetate and water were added and the organic layer was separated. The aqueous layer was extracted with ethyl acetate and the combined organic layer was washed with brine, dried over anhydrous sodium sulfate, and evaporated in vacuo to give tert-butyl 4-amino-5-(3-methoxyphenyl)valerate (245 mg).
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