Processes for synthesis of opiate alkaloid derivatives
AssigneeMallinckrodt Inc.
InventorsAnthony Mannino, James Zdrodowski
Life of this patent
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Abstract
The present invention provides processes for the synthesis of opiate alkaloids. In particular, the opiate alkaloids produced by the process of the invention are typically intermediate compounds that may be utilized to produce a variety of biologically active alkaloids including buprenorphine and diprenorphine.
Claims9
A process for the preparation of a compound of Formula (III), the process comprising a first reaction that comprises contacting a compound of Formula (I) with an aprotic solvent and a dienophile to form a compound of Formula (II), and then a second reaction that comprises contacting the compound of Formula (II) with a catalyst, hydrogen, and the aprotic solvent to form a compound of Formula (III) according to the following reaction scheme:
- wherein:
- R1 and R8 are independently selected from the group consisting of hydrocarbyl and substituted hydrocarbyl;
- R2 and R3 are independently selected from the group hydrogen, hydrocarbyl and substituted hydrocarbyl;
- R4 and R5 are independently selected from the group consisting of hydrogen, hydrocarbyl, substituted hydrocarbyl, halogen, {—}OH, {—}NH2, {—}SH, {—}SR8, and {—}OR8;
- R6 and R7 are independently selected from the group consisting of hydrogen, a protecting group, hydrocarbyl, and substituted hydrocarbyl;
- and
- X is oxygen, and
- wherein the first reaction and the second reaction are both conducted in a one-pot process;
- and the aprotic solvent used for the first reaction and the aprotic solvent for the second reaction are the same.
Dependencies are inferred from the claim text.