Decoration of the aromatic ring of dihydrocodeinone (hydrocodone) and 14-hydroxydihydrocodeinone (oxycodone).
Improved protocols for the preparation of 1-bromodihydrocodeinone (1-bromohydrocodone) and 1-bromo-14-hydroxydihydrocodeinone (1-bromooxycodone) and synthesis of the corresponding 1-chloro and 1-iodo derivatives have been achieved using the corresponding N-halosuccinimides in acidic milieu. The corresponding 1-carboethoxy derivative of 14-hydroxydihydrocodeinone (1-carboethoxyoxycodone) has been prepared by Pd-catalyzed reaction with carbon monoxide in ethanol. The ester was hydrolyzed to the corresponding zwitterionic amino acid.
Wilson
Michael L
ML
Department of Chemistry, Temple University, Philadelphia, Pennsylvania 19122, USA. michael.wilson@temple.edu
Carroll
Patrick J
PJ
Dalton
David R
DR
D000143:Acids; D001966:Bromine / Q000737:chemistry; D006853:Hydrocodone / Q000737:chemistry*; D004091:Hydromorphone / Q000031:analogs & derivatives / Q000737:chemistry; D007455:Iodine / Q000737:chemistry; D015394:Molecular Structure; D009294:Narcotics / Q000737:chemistry; D010098:Oxycodone / Q000737:chemistry*
D000143:Acids; D009294:Narcotics; C036083:morphinone; D006853:Hydrocodone; D007455:Iodine; D010098:Oxycodone; D004091:Hydromorphone; D001966:Bromine