N-t-butoxycarbonyl-(2-cyanophenyl)alanine → (S)-N-t-butyloxycarbonyl(2-aminomethylphenyl)alanine
Reaction equation
[C:1]([O:5][C:6]([N:8]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]#[N:21])[C@H:9]([C:11]([OH:13])=[O:12])[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2]>[Ni].CO>[C:1]([O:5][C:6]([N:8]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH2:20][NH2:21])[C@H:9]([C:11]([OH:13])=[O:12])[CH3:10])=[O:7])([CH3:2])([CH3:3])[CH3:4]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A mixture of (S)—N-t-butyloxycarbonyl(2-cyanophenyl)alanine (1.0 g), Raney® Nickel (1.0 g), and methanol (20 mL) was hydrogenated in a Parr apparatus at 50 psi for 60 h at room temperature. The catalyst was filtered and rinsed with methanol (20 mL three times). The combined filtrate and rinses were evaporated under vacuum, and the resulting residue was triturated with diethyl ether (30 mL five times) to obtain (S)—N-t-butyloxycarbonyl(2-aminomethylphenyl)alanine (406 mg).