Syntheses of p-diamines and p-amino alcohols : [an honors thesis (HONRS 499)]

Abstract

New synthetic routes to the preparations of (-diamines and (-amino alcohols have been realized. Excess methylamine combined with (-unsaturated ketone or aldehyde followed by reductive amination employing NaBH3CN or NaBH4 gave (-diamines in up to 50% yield. Thus, from crotonaldehyde, N, N1-dimethyl-1, 3-butanediamine was obtained. Similarly, methylamine combined with an (-unsaturated ketone or aldehyde followed by reduction with NaBH4 resulted in the preparation of (-amino alcohols. This reaction with 3-pentene-2-one produced 4-methylamino-2-pentanol. The likelihood of the reaction sequence consisting of initial addition across the double bond followed by reduction of the carbonyl group was indicated.