tert-Butyl(2E)-3-(3-amino-4-cyanophenyl)-2-methylacrylate → Tert-butyl 3-(3-amino-4-cyanophenyl)-2-methylpropanoate
Reaction equation
[NH2:1][C:2]1[CH:3]=[C:4](/[CH:10]=[C:11](\[CH3:19])/[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9]>C(OCC)(=O)C.[Pd]>[NH2:1][C:2]1[CH:3]=[C:4]([CH2:10][CH:11]([CH3:19])[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
1370 mg (5.3 mmol) of tert-butyl (2E)-3-(3-amino-4-cyanophenyl)-2-methylacrylate were dissolved in 30 ml of ethyl acetate, 282 mg of palladium on carbon (10%) were added and the mixture was stirred at RT under an atmosphere of hydrogen at atmospheric pressure for three days. The reaction mixture was then filtered off through celite, the filter residue was washed with ethyl acetate and the combined filtrate was concentrated. The crude product was purified by preparative HPLC (mobile phase acetonitrile/water). This gave 870 mg of the title compound (63% of theory).