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 860769Notes

Reaction equation

HRID 860769 reaction equation
[CH3:1][N:2]1[C@@H:18]2[CH2:19][C:7]3[CH:8]=[CH:9][C:10]([O:22][CH3:23])=[C:11]4[O:12][C@H:13]5[C:14]([O:20]C)=[CH:15][CH:16]=[C:17]2[C@:5]5([C:6]=34)[CH2:4][CH2:3]1.[OH:24]O.[OH-].[NH4+]>C(O)=O>[CH3:1][N:2]1[C@@H:18]2[CH2:19][C:7]3[CH:8]=[CH:9][C:10]([O:22][CH3:23])=[C:11]4[O:12][CH:13]5[C:14]([CH:15]=[CH:16][C@:17]2([OH:24])[C@:5]5([C:6]=34)[CH2:4][CH2:3]1)=[O:20]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 14923Ammonium HydroxideHCID 5324289Thebaine

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 149.6%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

Thebaine (100.0 g dry weight) was dissolved in 85% formic acid (252.3 g). 30% Hydrogen peroxide (43.6 g) was added over a period of about two hours. The mixture was stirred for three hours. Ammonium hydroxide solution was added to the mixture to increase the pH to 8–9. The solid precipitate was filtered and washed with water and ethanol. The solid was dried on the filter and in an oven. The product was 14-hydroxycodeinone (150.52 g damp, 75.32 g dry weight, 75% yield).

Workup

  1. temperatureto increase the pH to 8–9
  2. filtrationThe solid precipitate was filtered
  3. washwashed with water and ethanol
  4. customThe solid was dried on the
  5. filtrationfilter and in an oven

Sources & evidence

ORD record
ord-ff393624ab35474bbed7434ce81f8c4d
Source dataset
uspto-grants-2006_12
Patent number
US07153966B2

Reaction notes

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