Water → Thebaine

HRID 2289000Notes

Reaction equation

HRID 2289000 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].[CH3:23]C(C)([O-])C.[K+].O>CN(C)C=O.C(OCC)(=O)C>[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]([O:15][CH3:23])=[CH:16][CH:17]=[C:18]2[C@:5]5([C:6]=34)[CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 962WaterHCID 5459910CodeinoneHCID 23665647Potassium tert-butoxide

Product 1

HCID 5324289Thebaine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Codeinone (300 g) was added to a stirred suspension of potassium tert-butoxide (153 g) in N,N-dimethylformamide (5 ml) at room temperature. After 10 minutes, methyl trifluoromethanasulphonate (164 mg) was added dropwise to the suspension. The solution was stirred for 5 minutes, diluted with ethyl acetate (30 ml), and then poured into water (50 ml). The aqueous phase was removed, and the organic phase was dried with sodium sulphate and evaporated, producing an orange solid. Analysis by HPLC Against pure thebaine gave a thebaine content of 10%.

Workup

  1. additionmethyl trifluoromethanasulphonate (164 mg) was added dropwise to the suspension
  2. customThe aqueous phase was removed
  3. dry with materialthe organic phase was dried with sodium sulphate
  4. customevaporated
  5. customproducing an orange solid

Sources & evidence

ORD record
ord-0511df7feda94f6ca53db344690ef4d4
Source dataset
uspto-grants-2000_07
Patent number
US06090943

Reaction notes

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