HCID 13935580, compound → N-(4-benzyloxy-3,3-difluorobutyl)phthalimide

HRID 232164Notes

Reaction equation

HRID 232164 reaction equation
[CH2:1]([O:8][CH2:9][C:10]([F:19])([F:18])[CH2:11][CH2:12]OS(C)(=O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20]1(=[O:30])[NH:24][C:23](=[O:25])[C:22]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:21]12.[K]>CN(C=O)C>[CH2:1]([O:8][CH2:9][C:10]([F:19])([F:18])[CH2:11][CH2:12][N:24]1[C:23](=[O:25])[C:22]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:21]2[C:20]1=[O:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 13935580HCID 13935580, compoundHCID 24194345Phthalimide potassium salt

Product 1

HCID 13935581N-(4-benzyloxy-3,3-difluorobutyl)phthalimide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1-benzyloxy-2,2-difluoro-4-methanesulfonyloxybutane (63.44 g, 0.216 moles), potassium phthalimide (44 g, 0.238 moles) and dry DMF (500 mL), distilled from CaH2) is stirred and heated at 100° C. After a short time the mixture solidifies, and an additional dry DMF (500 mL) is added. Upon heating at 90°-100° C. for another 20 hours, salts are removed by filtration, and the DMF is distilled under vacuum (oil pump). The residue is dissolved in CH2Cl2 (800 mL) and washed with 1N KOH (twice) and 1N HCl (twice). Drying (Na2SO4) and evaporation yields N-(4-benzyloxy-3,3-difluorobutyl)-phthalimide as a yellow oil: 68.5 g (92%).

Workup

  1. distillationdistilled from CaH2)
  2. additionan additional dry DMF (500 mL) is added
  3. temperatureUpon heating at 90°-100° C. for another 20 hours
  4. customsalts are removed by filtration
  5. distillationthe DMF is distilled under vacuum (oil pump)
  6. dissolutionThe residue is dissolved in CH2Cl2 (800 mL)
  7. washwashed with 1N KOH (twice) and 1N HCl (twice)
  8. customDrying
  9. custom(Na2SO4) and evaporation

Sources & evidence

ORD record
ord-51c51fb0e110471eb6de3df94ff1f508
Source dataset
uspto-grants-1989_07
Patent number
US04851448

Reaction notes

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