HCID 58288264, compound → HCID 58288367, compound
Reaction equation
C([NH:8][C:9]1[CH:10]=[C:11]([CH2:16][C:17]([CH3:26])([CH3:25])[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH:12]=[CH:13][C:14]=1[Cl:15])C1C=CC=CC=1>C(OCC)(=O)C.[Pd]>[NH2:8][C:9]1[CH:10]=[C:11]([CH2:16][C:17]([CH3:26])([CH3:25])[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH:12]=[CH:13][C:14]=1[Cl:15]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
2.7 g (about 7.22 mmol) of tert-butyl 3-[3-(benzylamino)-4-chlorophenyl]-2,2-dimethylpropanoate were dissolved in 150 ml of ethyl acetate, and 100 ml of palladium on carbon (10%) were added. The reaction mixture was stirred at RT under an atmosphere of hydrogen at atmospheric pressure overnight. The mixture was then filtered off with suction through kieselguhr, the residue was washed thoroughly with ethyl acetate and the combined filtrate was concentrated. The crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 10:1→7:1). This gave 1.49 g (72.7% of theory) of the target compound.