(+/-)-Tert-butyl 3-[3-(benzylamino)-4-chlorophenyl]-2-cyclobutylpropanoate → (+/-)-Tert-butyl 3-(3-amino-4-chlorophenyl)-2-cyclobutylpropanoate
Reaction equation
C([NH:8][C:9]1[CH:10]=[C:11]([CH2:16][CH:17]([CH:25]2[CH2:28][CH2:27][CH2:26]2)[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][CH:17]([CH:25]2[CH2:26][CH2:27][CH2:28]2)[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
Procedure
1.85 g (4.63 mmol) of (+/−)-tert-butyl 3-[3-(benzylamino)-4-chlorophenyl]-2-cyclobutylpropanoate were dissolved in 10 ml of ethyl acetate and deoxygenated with argon, and 98 mg (0.093 mmol) of palladium on carbon (10%) were added. The reaction mixture was stirred at RT under an atmosphere of hydrogen at atmospheric pressure for 4 h and then allowed to stand over the weekend. The mixture was filtered through celite, the residue was washed with ethyl acetate, the filtrate was concentrated under reduced pressure and the residue of the filtrate was dried under high vacuum. This residue (about 1:1 mixture of starting material and target product) was once more dissolved in about 10 ml of ethyl acetate and deoxygenated with argon, and once more 98 mg (0.093 mmol) of palladium on carbon (10%) were added. Again, the reaction mixture was stirred at RT under an atmosphere of hydrogen at atmospheric pressure for 4 h. The mixture was then filtered through celite, the residue was washed with ethyl acetate, the filtrate was concentrated under reduced pressure and the residue was dried under high vacuum. Chromatographic purification on silica gel (mobile phase cyclohexane/ethyl acetate 20:1) gave 1.12 g of the target product (78.2% of theory).