Water → HCID 59370541, compound

HRID 2046664Notes

Reaction equation

HRID 2046664 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8](F)[C:7]([CH3:11])=[CH:6][C:3]=1[C:4]#[N:5].[OH:12][C@H:13]1[CH2:17][CH2:16][NH:15][C@H:14]1[CH3:18].C(=O)([O-])[O-].[Li+].[Li+].O>CS(C)=O>[Cl:1][C:2]1[CH:9]=[C:8]([N:15]2[CH2:16][CH2:17][C@H:13]([OH:12])[C@@H:14]2[CH3:18])[C:7]([CH3:11])=[CH:6][C:3]=1[C:4]#[N:5]

Participants

6

Reactant 4

HCID 962WaterHCID 11125Lithium CarbonateHCID 54198127HCID 54198127, compoundHCID 569655632-Chloro-4-fluoro-5-methylbenzonitrile

Product 1

HCID 59370541HCID 59370541, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
100 °C

Procedure

To a solution (25 mL) of 2-chloro-4-fluoro-5-methylbenzonitrile (848 mg) in dimethyl sulfoxide were added 0.9M-dimethyl sulfoxide solution (5.56 mL) of (2S,3S)-3-hydroxy-2-methylpyrrolidine and lithium carbonate (370 mg), and the mixture was stirred at 100° C. for 1 hr. Water was added 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 (developing solvent: hexane-ethyl acetate) and crystallized from ethyl acetate-hexane to give the title compound as a colorless solid (yield: 374 mg).

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 (developing solvent: hexane-ethyl acetate)
  6. customcrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-afb98ffd94cf45caa46347edd6007fcd
Source dataset
uspto-grants-2013_11
Patent number
US08592452B2

Reaction notes

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