Lithium Carbonate → HCID 59370514, compound

HRID 2046662Notes

Reaction equation

HRID 2046662 reaction equation
[OH:1][C:2]([C@H:5]1[CH2:9][CH2:8][NH:7][C@H:6]1[CH3:10])([CH3:4])[CH3:3].[Cl:11][C:12]1[C:19]([F:20])=[C:18](F)[CH:17]=[CH:16][C:13]=1[C:14]#[N:15].C(=O)([O-])[O-].[Li+].[Li+]>CS(C)=O>[Cl:11][C:12]1[C:19]([F:20])=[C:18]([N:7]2[CH2:8][CH2:9][C@H:5]([C:2]([OH:1])([CH3:4])[CH3:3])[C@@H:6]2[CH3:10])[CH:17]=[CH:16][C:13]=1[C:14]#[N:15]

Participants

5

Reactant 3

HCID 11125Lithium CarbonateHCID 216910522-Chloro-3,4-difluorobenzonitrileHCID 55299039(2S,3S)-3-(1-hydroxy-1-methylethyl)-2-methylpyrrolidine

Product 1

HCID 59370514HCID 59370514, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of (2S,3S)-3-(1-hydroxy-1-methylethyl)-2-methylpyrrolidine 1/2 oxalate (639 mg), 2-chloro-3,4-difluorobenzonitrile (491 mg), lithium carbonate (669 mg) and dimethyl sulfoxide (13 mL) was stirred at 90° C. for 1 hr. The reaction mixture was cooled and partitioned between water and ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated. The obtained residue was purified by silica gel column chromatography (developing solvent: ethyl acetate-hexane). The obtained solid was recrystallized from ethyl acetate to give the title compound as crystals (yield: 538 mg).

Workup

  1. temperatureThe reaction mixture was cooled
  2. custompartitioned between water and ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe obtained residue was purified by silica gel column chromatography (developing solvent: ethyl acetate-hexane)
  7. customThe obtained solid was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-f3a7431aafa746d48bc2aa22635d78ff
Source dataset
uspto-grants-2013_11
Patent number
US08592452B2

Reaction notes

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