
TY  - JOUR
A1  - Gore, J 
A1  - Kasum, B 
A1  - Holman, MA 
A1  - Scharfbillig, IM 
A1  - Ward, AD 
T1  - The Structure of a Human Metabolite of Pholcodine
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1996
VL  - 49
IS  - 11
SP  - 1235
EP  - 1242
KW  - 
UR  - https://doi.org/10.1071/CH9961235 
N2  - 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. 
ER  -

