Peracetic Acid → Peracetic Acid

HRID 1385612Notes

Reaction equation

HRID 1385612 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].[C:23]([O:26][OH:27])(=[O:25])[CH3:24]>CCOCC>[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:25])[C@:5]5([C:6]=34)[CH2:4][CH2:3]1)=[O:15].[C:23]([O:26][OH:27])(=[O:25])[CH3:24]

Participants

5

Reactant 2

HCID 6585Peracetic AcidHCID 5459910Codeinone

Product 2

HCID 6585Peracetic AcidHCID 5359420(4R,4aS,12bS)-4a-hydroxy-9-methoxy-3-methyl-2,4,7a,13-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

14-Hydroxycodeinone was synthesized from the dienolsilyl ether of codeinone by oxidative hydroxylation using a peracetic acid solution preparation. The peracetic acid solution was prepared as follows:

Sources & evidence

ORD record
ord-1f680308c09748249ba34937cf42c9af
Source dataset
uspto-grants-2001_07
Patent number
US06262266B1

Reaction notes

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