Water → HCID 178502737, compound

HRID 1506134Notes

Reaction equation

HRID 1506134 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([C:8]([N:10]([O:12][CH3:13])[CH3:11])=[O:9])[CH2:4][CH2:3]1.[H-].[Na+].[CH3:16]I.O>CN(C)C=O>[CH3:13][O:12][N:10]([CH3:11])[C:8]([C@H:5]1[CH2:6][CH2:7][C@H:2]([O:1][CH3:16])[CH2:3][CH2:4]1)=[O:9]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178502734HCID 178502734, compound

Product 1

HCID 178502737HCID 178502737, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

trans-4-Hydroxy-N-methoxy-N-methylcyclohexanecarboxamide (536 mg, 2.86 mmol) in N,N-dimethylformamide (5 mL) was mixed with sodium hydride (55 wt % dispersion in mineral oil, 150 mg, 3.44 mmol) and methyl iodide (214 μL, 3.44 mmol) under cooling with ice and stirred for 3 hours while the temperature was gradually raised to room temperature. After addition of water, the reaction mixture was extracted with ethyl acetate, and the organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/2→1/1 (v/v)) to give the title compound as a colorless oil (556 mg, yield 97%).

Workup

  1. temperatureunder cooling with ice
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washthe organic layer was washed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/2→1/1 (v/v))

Sources & evidence

ORD record
ord-c2e2ceb7673f4c38a7493c24ab548141
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

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