Allyl bromide → HCID 53728063, compound

HRID 1389897Notes

Reaction equation

HRID 1389897 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:7][C@H:8]3[NH:19][CH2:18][CH2:17][C@@:14]4([C:15]=2[CH:16]=1)[C@H:9]3[CH2:10][C:11]([CH3:21])([CH3:20])[O:12][CH2:13]4.[CH2:22](Br)[CH:23]=[CH2:24].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:24]([N:19]1[CH2:18][CH2:17][C@@:14]23[C:15]4[CH:16]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=4[CH2:7][C@@H:8]1[C@@H:9]2[CH2:10][C:11]([CH3:21])([CH3:20])[O:12][CH2:13]3)[CH:23]=[CH2:22]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 54382549HCID 54382549, compound

Product 1

HCID 53728063HCID 53728063, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-methoxy-7,7-dimethyl-6-oxamorphinan (XI, prepared in Example 3) (0.005 m), allyl bromide (0.006 m) and potassium carbonate (2 g) in 20 ml of acetonitrile is heated at reflux for 18 hours. The mixture is filtered and the filtrate concentrated. The residue is treated with water and extracted with ethyl acetate. The extracts are dried (Na2SO4) and concentrated to give the title compound.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 18 hours
  3. filtrationThe mixture is filtered
  4. concentrationthe filtrate concentrated
  5. additionThe residue is treated with water
  6. extractionextracted with ethyl acetate
  7. dry with materialThe extracts are dried (Na2SO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-b7b827e4df1847efb9913c83711fdd12
Source dataset
uspto-grants-1981_01
Patent number
US04246413

Reaction notes

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