N-demethylation of N-methyl morphinans
AssigneeMallinckrodt Inc.
InventorsPeter X. Wang, Tao Jiang, Gary L. Cantrell, David W. Berberich
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Abstract
The present invention provides a synthetic process for the N-demethylation of N-methyl morphinans. In particular, the invention provides improved synthetic methods for the preparation of N-demethylated morphinan compounds that may be employed as starting materials, for example, commonly available N-methyl opiates such as oripavine and thebaine, and C(3)-protected hydroxy derivatives of oripavine.
Claims20
A process for preparing a compound comprising Formula 2 from a compound comprising Formula 1 according to the following reaction:
- wherein:
- R1 is selected from the group consisting of hydrogen, hydrocarbyl, and substituted hydrocarbyl;
- R2, R3, and R4 are independently selected from the group consisting of hydrogen, halogen, hydroxyl, {—}OR8, hydrocarbyl, and substituted hydrocarbyl;
- R6 is an atom selected from the group consisting of oxygen and nitrogen;
- R8 is selected from the group consisting of hydrocarbyl and substituted hydrocarbyl;
- L is halogen;
- Y is an atom selected from the group consisting of oxygen, nitrogen and sulfur;
- Z is selected from the group consisting of hydrocarbyl and substituted hydrocarbyl;
- and
- n is 1 or 2.
An N-carboxylic acid ester morphinan derivative comprising Formula 2:
- wherein
- R3 is selected from the group consisting of methyl, —C(O)OZ, and a hydroxy protecting group, and
- Z is selected from the group consisting of hydrocarbyl and substituted hydrocarbyl.
Dependencies are inferred from the claim text.