Water → HCID 67389612, compound

HRID 907030Notes

Reaction equation

HRID 907030 reaction equation
C1([C@]2(O)[CH2:8][CH2:7][NH:6][C@H:5]2[CH:9]([CH3:11])[CH3:10])CC1.F[C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[C:16]([O:22][CH3:23])[CH:15]=1.[C:24](=[O:27])([O-])[O-].[Li+].[Li+].O>CS(C)=O>[OH:27][C@H:24]1[C:9]([CH3:11])([CH3:10])[CH2:5][N:6]([C:14]2[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[C:16]([O:22][CH3:23])[CH:15]=2)[C@@H:7]1[CH3:8]

Participants

6

Reactant 4

HCID 962WaterHCID 11125Lithium CarbonateHCID 27833294-Fluoro-2-methoxybenzonitrileHCID 59273011(2S,3R)-3-cyclopropyl-2-isopropylpyrrolidin-3-ol

Product 1

HCID 67389612HCID 67389612, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A suspension (5 mL) of (2R,3S)-2,4,4-trimethylpyrrolidin-3-ol 0.5 oxalate (152 mg), 4-fluoro-2-methoxybenzonitrile (183 mg) and lithium carbonate (155 mg) in DMSO was stirred at 100° C. for 15 hr, added to water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=50/1→2/3) to give the title compound as a colorless solid (yield: 103 mg, yield: 45%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=50/1→2/3)

Sources & evidence

ORD record
ord-26b0d105c5e940b78d00bfb10b97e641
Source dataset
uspto-grants-2011_09
Patent number
US08013008B2

Reaction notes

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