N-(3-methyl-2-nitrobenzyl)-L-alanine ethyl ester → N-(2-amino-3-methylbenzyl)-L-alanine ethyl ester

Reaction equation

[CH2:1]([O:3][C:4](=[O:19])[C@H:5]([CH3:18])[NH:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[C:9]=1[N+:15]([O-])=O)[CH3:2].[H][H]>C(O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:19])[C@H:5]([CH3:18])[NH:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[C:9]=1[NH2:15])[CH3:2]

Participants

Procedure

A solution of 26.6 g of N-(3-methyl-2-nitrobenzyl)-L-alanine ethyl ester in 100 ml of absolute ethanol was hydrogenated in the presence of 2 g of 10% palladium/carbon. 6.7 liters of hydrogen were taken up in 5 hours. After completion of the hydrogenation, the catalyst was filtered off and the filtrate was evaporated to dryness. There was obtained N-(2-amino-3-methylbenzyl)-L-alanine ethyl ester in the form of a yellow oil; [α]D =-52.6° (c=1% in methanol).