Robert Darrin Wilson

A new synthesis of 1,2,4-triazolin-5-ones: application to the convergent synthesis of an NK1 antagonist

Abstract Chlorotriazolinone 4 has been synthesised in a single step via the novel condensation of semicarbazide hydrochloride with orthoester 8 . Alkylation of secondary amine 3 with compound 4 proceeds in 99% yield to afford the target NK 1 antagonist 1 .

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

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.