[CH:1]([O-:3])=[O:2].[NH4+:4].N1CCCC(C(OCC2([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([O:26][CH3:27])=[O:25])[CH:19]=3)C=CC=CC2)=O)C1>[Pd].CO>[CH3:27][O:26][C:24]([C:20]1[CH:19]=[C:18]([N:4]2[CH2:22][CH2:23][CH2:18][CH:19]([C:1]([OH:3])=[O:2])[CH2:20]2)[CH:23]=[CH:22][CH:21]=1)=[O:25]In an argon atmosphere, 10% palladium on activated carbon (234 mg) and ammonium formate (1.66 g, 26.4 mmol) were added to 1-[3-(methoxycarbonyl)phenyl]benzyl nipecotate (2.34 g, 6.60 mmol) in methanol (50 mL). The reaction mixture was stirred at room temperature for 4 hours. Subsequently, the mixture was filtered through Celite and the filtrate was concentrated. 5% aqueous citric acid was added to the residue and the mixture was extracted with ethyl acetate. The organic layer was then washed with brine and was dried over sodium sulfate. The solvent was evaporated to give 1.57 g (90%) of the desired compound as a pale reddish brown powder.
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