Reductive Amination of Pyruvate Esters: A Microscale Synthesis of N-Benzylalanine Esters

TCE

The Chemical Educator

ISSN: 1430-4171 (electronic version)

Table of Contents

Abstract Volume 3 Issue 3(1998), S1430-4171(98)03205-8

Reductive Amination of Pyruvate Esters: A Microscale Synthesis of N-Benzylalanine Esters

R. David Crouch*, Michael S. Holden*, and Tom M. Weaver

Dickinson College, Carlisle, PA 17013-2896

Published online: 1 June 1998

Abstract. 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.

Key Words: Laboratories and Demonstrations; molecular modeling; NMR; reductive amination; IR spectroscopy; infrared spectroscopy

(*) Corresponding author. (E-mail: crouch@dickinson.edu; holden@dickinson.edu)

Article in PDF format (74 KB )

Supporting Materials:

Supporting documentation. Project leader instructions (12 KB) 10.1007/s0089798205b

Student handout with IR spectra (872 KB) 10.1007/s0089798205c