Water → HCID 24986663, compound

HRID 906981Notes

Reaction equation

HRID 906981 reaction equation
[CH3:1][C@H:2]1[C@@:6]([CH3:8])([OH:7])[CH2:5][CH2:4][NH:3]1.[F:9][C:10]1[CH:17]=[C:16](F)[CH:15]=[CH:14][C:11]=1[C:12]#[N:13].C(=O)([O-])[O-].[Li+].[Li+].O>CS(C)=O>[F:9][C:10]1[CH:17]=[C:16]([N:3]2[CH2:4][CH2:5][C@@:6]([OH:7])([CH3:8])[C@@H:2]2[CH3:1])[CH:15]=[CH:14][C:11]=1[C:12]#[N:13]

Participants

6

Reactant 4

HCID 962WaterHCID 11125Lithium CarbonateHCID 775452,4-DifluorobenzonitrileHCID 59556870(2S,3S)-2,3-dimethylpyrrolidin-3-ol

Product 1

HCID 24986663HCID 24986663, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution (2 mL) of (2S,3S)-2,3-dimethylpyrrolidin-3-ol 0.5 oxalate (228 mg), 2,4-difluorobenzonitrile (292 mg) and lithium carbonate (206 mg) in DMSO was stirred at 80° C. for 18 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=9:1→2:1) and recrystallized from hexane-isopropyl ether to give the title compound as a colorless solid (yield: 188 mg, yield: 57%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=9:1→2:1)
  6. customrecrystallized from hexane-isopropyl ether

Sources & evidence

ORD record
ord-3596dd5b86544e2baebcd801e2eccfac
Source dataset
uspto-grants-2011_09
Patent number
US08013008B2

Reaction notes

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