Water → HCID 59273050, compound

HRID 907040Notes

Reaction equation

HRID 907040 reaction equation
F[C:2]1[CH:9]=[C:8]([N:10]2[C@H:14]([CH3:15])[CH2:13][C@@:12]([OH:17])([CH3:16])[C@@H:11]2[CH3:18])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH3:19][O-:20].[Na+].O>CS(C)=O>[OH:17][C@@:12]1([CH3:16])[CH2:13][C@@H:14]([CH3:15])[N:10]([C:8]2[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[C:2]([O:20][CH3:19])[CH:9]=2)[C@H:11]1[CH3:18]

Participants

5

Reactant 3

HCID 962WaterHCID 10942334Sodium Methoxide2×HCID 59273019HCID 59273019, compound

Product 1

HCID 59273050HCID 59273050, compoundYield 50.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution (5 mL) of 2-fluoro-4-[(2S,3S,5R)-3-hydroxy-2,3,5-trimethylpyrrolidin-1-yl]benzonitrile (47.6 mg) in DMSO was added sodium methoxide (35 mg) and the mixture was stirred at 100° C. for 3.5 hr. Sodium methoxide (130 mg) was added, and the mixture was stirred at 100° C. for 4.5 hr. The reaction mixture was 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: 25.1 mg, yield: 50%).

Workup

  1. stirringthe mixture was stirred at 100° C. for 4.5 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=50/1→2/3)

Sources & evidence

ORD record
ord-b60b4af7ffca42aea42302e3fd7ac7a5
Source dataset
uspto-grants-2011_09
Patent number
US08013008B2

Reaction notes

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