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

HRID 1436845Notes

Reaction equation

[CH3:1][N:2]1[C@@H:19]2[CH2:20][C:7]3[CH:8]=[CH:9][C:10]([O:21][CH3:22])=[C:11]4[O:12][C@H:13]5[C:14]([CH:16]=[CH:17][C@@H:18]2[C@:5]5([C:6]=34)[CH2:4][CH2:3]1)=[O:15].[OH:23]O>>[CH3:1][N:2]1[C@@H:19]2[CH2:20][C:7]3[CH:8]=[CH:9][C:10]([O:21][CH3:22])=[C:11]4[O:12][CH:13]5[C:14]([CH:16]=[CH:17][C@:18]2([OH:23])[C@:5]5([C:6]=34)[CH2:4][CH2:3]1)=[O:15]

Participants

Reactant 2

HCID 784Hydrogen Peroxide

HCID 5459910Codeinone

Product 1

HCID 5359420(4R,4aS,12bS)-4a-hydroxy-9-methoxy-3-methyl-2,4,7a,13-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-oneYield 57%

Procedure

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)).

Sources & evidence

ORD record: ord-1241605b55a2416a8d579e7ae85295d3
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07619087B2

Reaction notes

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