Hydrochloric Acid → HCID 86737788, compound

HRID 1680230Notes

Reaction equation

HRID 1680230 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:6][C@H:7]3[NH:18][CH2:17][CH2:16][C@@:13]4([C:14]=2[CH:15]=1)[C@@:8]3([O:21][CH3:22])[C@H:9]([CH3:20])[CH2:10][C:11](=[O:19])[CH2:12]4.[CH3:23][C:24]([CH3:28])=[CH:25][CH2:26]Br.[ClH:29]>C(O)C>[ClH:29].[CH3:23][C:24]([CH3:28])=[CH:25][CH2:26][N:18]1[CH2:17][CH2:16][C@@:13]23[C:14]4[CH:15]=[C:2]([OH:1])[CH:3]=[CH:4][C:5]=4[CH2:6][C@@H:7]1[C@:8]2([O:21][CH3:22])[C@H:9]([CH3:20])[CH2:10][C:11](=[O:19])[CH2:12]3

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 700922-Butene, 1-bromo-3-methyl-HCID 70569023HCID 70569023, compound

Product 1

HCID 86737788HCID 86737788, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-hydroxy-14-methoxy-8α methylmorphinan-6-one (27) (0.13 g, 0.43 mmol), dimethylallyl bromide (0.125 g, 0.84 mmol) and ethanol (10 ml) was refluxed under a nitrogen atmosphere for 16 hours (oil bath temperature 105°-110° C). The mixture was filtered and the residue washed with ethanol. The filtrate upon concentration gave a solid product which was chromatographed over silica gel using graded methanol/chroloform mixtures as the eluant. Fractions containing the desired product were collected and evaporated to give total of 0.02 g (12.6% theory) of pure product. An additional 0.026 g of less pure 28 was also obtained. The pure material was converted into the HCl salt by treatment with ethereal HCl.

Workup

  1. temperaturewas refluxed under a nitrogen atmosphere for 16 hours (oil bath temperature 105°-110° C)
  2. filtrationThe mixture was filtered
  3. washthe residue washed with ethanol
  4. concentrationThe filtrate upon concentration
  5. customgave a solid product which
  6. customwas chromatographed over silica gel using graded methanol/chroloform mixtures as the eluant
  7. additionFractions containing the desired product
  8. customwere collected
  9. customevaporated
  10. customto give total of 0.02 g (12.6% theory) of pure product
  11. customAn additional 0.026 g of less pure 28 was also obtained

Sources & evidence

ORD record
ord-cd9d4d0f65b841cdbc61572c30f93a5e
Source dataset
uspto-grants-1981_06
Patent number
US04272540

Reaction notes

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