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Oxycodone

CH3O

O HO O H N

14-hydroxydihydrocodeinone Oxycodone HCl • Oxynorm® - Nppp o Tablets • Oxycontin® - Napp o Tablets

Oxycodone terephthalate Endodan® - (US only) Tablets
CH3O COO−

O HO O H N+ H COO−

oxycodone terephthalate

2

Oxycodone synthesis
hydrogen peroxide
O H O O O H N O OH OCH3 OH

H O CH3O N O H CH3O N

O H

OCH3

HCOOH, H2O2, H2O iPrOH, 0-5oC, 2h, o then 45 C, 3h 1,4-addition H+
CH3O

thebaine

OCH3

OCH3

WO Patent 2004108090
CH3O CH3O

O HO O H N

H2, 5% Pd/C 30-40 psi, rt, 20h

O HO O H N

− MeOH

O H N

HO hemiketal hydrolysis CH3O OH

oxycodone o m.p. 218-220 C EtOH conc HCl in iPrOH

14-hydroxycodeinone 90% yield

oxycodone HCl m.p. 270-272oC (dec.)

Alternative synthesis of 14-hydroxycodeinone intermediate

O O CH3O Cl N O H CH3O N O OCH3 O H Cl

mCPBA mCPBA AcOH/CF3COOH heat 1,4-addition
CH3O N

O

O

O

OH OCH3

thebaine aq. H
Cl
+

OCH3 OH N O OH OH OCH3

OCH3

O

O HO CH3O OH H N

OCH3

CH3O

aq. H+

J. Med. Chem., 1974, 17, 1117
O HO O H N

− MeOH hemiketal hydrolysis

14-hydroxycodeinone