The unexpected formation of N-benzylated tertiary amines from their corresponding CBZ-protected precursors Original Research Article

The unexpected formation of N-benzyl tertiary amines was observed during the hydrogenolysis of their corresponding CBZ-protected secondary amines, indicating a potential problem for the industrial application of a process otherwise thought to be robust. The reaction is favoured by low hydrogen availability, and under such conditions competitive formation of N-benzyl analogues occurs rather than affording exclusively the expected free amine.