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

HRID 2072878Notes

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

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

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

Sources & evidence

ORD record: ord-c8d504af9a8848b3a07481918d0c2343
Source dataset: uspto-grants-1990_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04914240

Reaction notes

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