
%0 Journal Article
%A Gore, J 
%A Kasum, B 
%A Holman, MA 
%A Scharfbillig, IM 
%A Ward, AD 
%T The Structure of a Human Metabolite of Pholcodine
%J Australian Journal of Chemistry
%D 1996/11/01
%V 49
%N 11
%P 1235-1242
%K 
%R https://doi.org/10.1071/CH9961235
%U https://www.publish.csiro.au/paper/CH9961235 
%X The structure of a metabolite of pholcodine produced by humans is shown, by spectroscopic and synthetic data, to be a morpholin-3-one (amide) derivative rather than the alternative morpholin-2-one ( lactone ) isomer. Acylation of diethanolamine leads to an N,O- diacyl product even when only 1 equiv. of acylating agent is used. A mechanism is proposed to account for this observation. The appropriately substituted diacyl product can be cyclized to give a morpholin-3-one derivative which can be coupled to morphine by using caesium carbonate to give the metabolite. Suitable morpholin-2-one systems were coupled with morphine in basic conditions to give the alternative metabolite structure whose lactone group hydrolysed on standing to form a hydroxy acid derivative. 
