The goal of this research was to synthesize secondary amines with other functional groups or steric bulk near the nitrogen atom. The relative rate of reaction with an isocyanate can then be measured and the effect of the nearby groups determined. The amines were made using two synthetic strategies, either a Michael addition or a reductive amination. When utilizing a reductive amination, the common reducing agent sodium triacetoxyborohydride was used and found to work well even in the presence of esters. In the compounds where esters were present after the amine was synthesized the esters were converted cleanly and efficiently to amides using a catalytic amount of triazabicyclodecene (TBD) in a microwave reactor. The relative rates of reaction of the amines with an isocyanate were then measured by competitive experiments using 1H NMR.

Synthesis of secondary amines

249th National Meeting (2015)

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