Water → Thebaine

HRID 840345

Reaction equation

HRID 840345 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+].FC(F)(F)S(OC)(=O)=O.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

7

Reactant 4

HCID 962WaterHCID 9526Methyl triflateHCID 5459910CodeinoneHCID 23665647Potassium tert-butoxide

Product 1

HCID 5324289Thebaine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Codeinone (300 mg) was added to a stirred suspension of potassium tert-butoxide (153 mg) in N,N-dimethylformamide (5 ml) at room temperature. After 10 minutes, methyl trifluoromethanesulphonate (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. customThe aqueous phase was removed
  2. dry with materialthe organic phase was dried with sodium sulphate
  3. customevaporated
  4. customproducing an orange solid

Sources & evidence

ORD record
ord-d2e322c4d0dd4e6dabaf0efbdbcd0e09
Source dataset
uspto-grants-2002_04
Patent number
US06365742B1

Linked notes

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