HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrogen Peroxide → (4R,4aS,12bS)-4a-hydroxy-9-methoxy-3-methyl-2,4,7a,13-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrogen Peroxide | HCID 784 | — |
| Reactant | Codeinone | HCID 5459910 | — |
| Product | (4R,4aS,12bS)-4a-hydroxy-9-methoxy-3-methyl-2,4,7a,13-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one | HCID 5359420 | 57% |
Reaction Steps
Oxidation of codeinone (VI) by action of peroxoacids, of combination of organic acids and hydrogen peroxide, or of inorganic oxidizing agents (e.g. Co3+ salts), with a maximum yield of 57% of 14β-hydroxycodeinone, which is hydrogenated to Oxycodone (I) (Coop A., Rice K. C.: Tetrahedron 55, 11429 (1999)).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07619087B2 |
| Source dataset | uspto-grants-2009_11 |
| ORD ID | ord-1241605b55a2416a8d579e7ae85295d3 |
| Source note | uspto-grants-2009_11 |