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Large quantities of pure glycamines were conveniently prepared by the reductive alkylation of ammonia or by the hydrogenolysis of N-benzylglycamines. To ensure high quality products, purification of the glycamines from either process should be carried out through their Schiff bases.Although 1-amino-l-deoxy sugars, the glycamines, have been known for over fifty years, a good preparative method which is practical for the synthesis of large quantities of high purity material is not available. The need for large quantities of galactamine of greater than 95% purity as a resolving agent in a synthesis of pantothenic acid2 prompted us to reinvestigate the preparation of this class of compounds.Glycamines previously have been prepared by the chemical reduction of sugar oximes,3-5 by electrolytic, chemical and catalytic reduction of gly-cosylamines5 and by the reductive alkylation of ammonia with a sugar.6-8 The chemical and electrolytic reduction methods were of little interest because they were not readily adaptable to large-scale operations. The Flint and Salzburg7 method yielded impure sirups unsuitable for our purposes.

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