Diethyl Sulfate → Methyl 1-ethyl-2-methyl-6-oxo-4-[4-(trifluoromethyl)phenyl]-1,4,5,6-tetrahydro-3-pyridinecarboxylate

HRID 734762Notes

Reaction equation

HRID 734762 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][C:13](=[O:15])[NH:12][C:11]([CH3:16])=[C:10]2[C:17]([O:19][CH3:20])=[O:18])=[CH:5][CH:4]=1.[H-].[Na+].S(OCC)(O[CH2:29][CH3:30])(=O)=O>CN(C=O)C.O>[CH2:29]([N:12]1[C:13](=[O:15])[CH2:14][CH:9]([C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:21])([F:1])[F:22])=[CH:8][CH:7]=2)[C:10]([C:17]([O:19][CH3:20])=[O:18])=[C:11]1[CH3:16])[CH3:30]

Participants

6

Reactant 3

HCID 6163Diethyl SulfateHCID 24758Sodium hydrideHCID 2854419HCID 2854419, compound

Product 1

HCID 68825985Methyl 1-ethyl-2-methyl-6-oxo-4-[4-(trifluoromethyl)phenyl]-1,4,5,6-tetrahydro-3-pyridinecarboxylateYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The product from Example 5, Step 1 (0.627 g, 2.00 mmol, 1.00 equiv) was dissolved in DMF (9 mL) and sodium hydride (60% dispersion in mineral oil, 0.112 g, 1.40 equiv) was added. After the reaction had stirred for 20 minutes at room temperature, diethyl sulfate (0.314 mL, 2.40 mmol, 1.20 equiv) was added and the reaction was heated to 100° C. for 4 hours. The reaction was diluted with H2O and extracted with EtOAc. The organic phase was washed four times with H2O and once with satd. NaCl, dried over MgSO4 and concentrated en vacuo to provide 0.627 g (92%) of the title compound as an oil. MS (ES+) m/e 342 [M+H]+

Workup

  1. temperaturethe reaction was heated to 100° C. for 4 hours
  2. extractionextracted with EtOAc
  3. washThe organic phase was washed four times with H2O
  4. dry with materialNaCl, dried over MgSO4
  5. concentrationconcentrated en vacuo

Sources & evidence

ORD record
ord-387b6c27c0b64639a80acf6e02418c8b
Source dataset
uspto-grants-2009_09
Patent number
US07592357B2

Reaction notes

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