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
Reaction equation
C(O)(=O)C(O)=[O:3].[CH3:7][N:8]1[C@@H:24]2[CH2:25][C:13]3[CH:14]=[CH:15][C:16]([O:28][CH3:29])=[C:17]4[O:18][C@H:19]5[C:20]([O:26]C)=[CH:21][CH:22]=[C:23]2[C@:11]5([C:12]=34)[CH2:10][CH2:9]1.OO.P([O-])([O-])([O-])=O.[OH-].[K+]>O.C(O)=O>[CH3:7][N:8]1[C@@H:24]2[CH2:25][C:13]3[CH:14]=[CH:15][C:16]([O:28][CH3:29])=[C:17]4[O:18][CH:19]5[C:20]([CH:21]=[CH:22][C@:23]2([OH:3])[C@:11]5([C:12]=34)[CH2:10][CH2:9]1)=[O:26]Participants
8
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 5 °C
Procedure
18.66 kg of oxalic acid is dissolved in water, 84.8 kg of thebaine is added, and after it has dissolved, 19.50 kg of 88% formic acid and 42.4 kg of 30% hydrogen peroxide are added. The reaction mixture is stirred at 25° C. until total conversion of thebaine (determined by capillary electrophoresis; capillary 50 cm×0.05 mm, electrolyte 100 mM TRJS/phosphate, pH 2.7, 5 mM dimethoxy-β-cyclodextrin, temperature 25° C. 30 kV; thebaine migration time 5.6 min). The reaction mixture is cooled down to 5° C., 10% aqueous solution of KOH is added with stirring until pH of 9.2. Precipitated crystals of 14-hydroxycodeinone are centrifuged off, washed with water and dried. Ca. 76 kg of 14-hydroxycodeinone (89%) is obtained.
Workup
- dissolutionafter it has dissolved
- customPrecipitated crystals of 14-hydroxycodeinone
- washwashed with water
- customdried
Sources & evidence
- ORD record
- ord-0485b392235f4ab2bcbf68bf8c42cd21
- Source dataset
- uspto-grants-2009_11
- Patent number
- US07619087B2
Reaction notes
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