Patent ID: 6790959
Filing Date: 2004-09-14
Classification: C07D

Abstract:
A process for commercially manufacturing thebaine which comprises the steps of:(a) converting codeine or a codeine salt into the intermediate N-carboalkoxynorcodeine or N-carboaryloxynorcodeine by reacting the codeine or codeine salt with a chloroformate in the presence of an alkali metal carbonate or alkali metal bicarbonate and an inert solvent at a temperature of about 0 to about 85Â° C.; (b) oxidizing the intermediate N-carboalkoxynorcodeine or N-carboaryloxynorcodeine to yield N-carboalkoxynorcodeinone or N-carboaryloxynorcodeinone using an oxidizing agent in the presence of an inert solvent at a temperature of about 0 to about 60Â° C.; (c) enolizing the intermediate N-carboalkoxynorcodeine or N-carboaryloxynorcodeine with a base in an inert solvent at a temperature of about âˆ’20 to about 50Â° C., and methylating the resultant enolate salt with a methylating agent in an inert solvent at a temperature of about âˆ’20 to about 50Â° C.; and (d) reducing the intermediate N-carboalkoxynorthebaine or N-carboaryloxynorthebaine to yield thebaine using a reducing agent in the presence of an inert solvent.