The reductive amination of pyruvate esters using benzylamine and sodium triacetoxyborohydride is described. Students isolate the N-benzylalanine ester and determine its structure using NMR and IR spectroscopy. Computational methods using CAChe provide information on reactive sites in the pyruvate substrate and reaction intermediates and allow for insight into the reaction mechanism. This experiment is safer than the more traditional reductive amination techniques, and it is appropriate for the introductory organic laboratory.
Crouch et al. (Mon,) studied this question.