Cleavage of tertiary bases with phenyl chloroformate: the reconversion of 21-deoxyajmaline into ajmaline

Abstract

An efficient general procedure for the cleavage of tertiary amines, involving their reaction with phenyl chloroformate under mild conditions, gives the corresponding phenyl N-carboxylates in high yield. Cleavage of deoxyajmaline with this reagent in the presence of lithium iodide affords phenyl 21-iododihydrochanoajmaline N(b)-carboxylate, which has been further converted into ajmaline, thus completing a Partial SYNTHESIS Of ajmaline from deoxyajmalal-A.