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
[OH:1]O.[CH3:3][N:4]1[C@@H:20]2[CH2:21][C:9]3[CH:10]=[CH:11][C:12]([O:24][CH3:25])=[C:13]4[O:14][C@H:15]5[C:16]([O:22]C)=[CH:17][CH:18]=[C:19]2[C@:7]5([C:8]=34)[CH2:6][CH2:5]1>>[CH3:3][N:4]1[C@@H:20]2[CH2:21][C:9]3[CH:10]=[CH:11][C:12]([O:24][CH3:25])=[C:13]4[O:14][CH:15]5[C:16]([CH:17]=[CH:18][C@:19]2([OH:1])[C@:7]5([C:8]=34)[CH2:6][CH2:5]1)=[O:22]Participants
Procedure
A 0.10 L round bottom flask (RBF) is charged with 18.9 g of formic acid, 9.9 g of water, and 7.8 g of 2-propanol. This mixture is stirred at 20–30° C. for 5 minutes. Into this solution is added 5.0 g of thebaine bitartrate monohydrate. This is stirred magnetically at room temperature for 10 minutes until dissolution is achieved. The color of the solution depends on the quality of the thebaine bitartrate. Good quality of thebaine bitartrate affords a pale yellowish solution. No exothermic effect is observed. The solution is cooled in an ice-bath for 20 minutes, and then into this solution 1.29 g of hydrogen peroxide is added. The resulting solution is stirred in the ice-bath for one hour. The ice-bath is removed, and an oil-bath with temperature controller is applied to the reaction flask. Heating is started and the temperature of the reaction mixture is kept at 45° C. for 3 h (completion of reaction tested by HPLC; residual thebaine <0.5 a/a %).
Workup
- temperatureThe solution is cooled in an ice-bath for 20 minutes
- customThe ice-bath is removed
- customan oil-bath with temperature controller is applied to the reaction flask
- temperatureHeating
- custom(completion of reaction
Sources & evidence
- ORD record
- ord-b2a9f41eff9c4c85a0dfe07c22329aa1
- Source dataset
- uspto-grants-2006_07
- Patent number
- US07071336B2
Reaction notes
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