Imidazole → 4-(tert-butyldimethylsilyloxy)-N-methoxy-N-methylcyclohexanecarboxamide

HRID 1506136Notes

Reaction equation

HRID 1506136 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][CH:5]([C:8]([N:10]([O:12][CH3:13])[CH3:11])=[O:9])[CH2:4][CH2:3]1.N1C=CN=C1.[C:19]([Si:23](Cl)([CH3:25])[CH3:24])([CH3:22])([CH3:21])[CH3:20].O>CN(C)C=O>[Si:23]([O:1][CH:2]1[CH2:7][CH2:6][CH:5]([C:8]([N:10]([O:12][CH3:13])[CH3:11])=[O:9])[CH2:4][CH2:3]1)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:25])[CH3:24]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 86642922HCID 86642922, compound

Product 1

HCID 231446014-(tert-butyldimethylsilyloxy)-N-methoxy-N-methylcyclohexanecarboxamideYield 73.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Hydroxy-N-methoxy-N-methylcyclohexanecarboxamide (7.34 g, 39.2 mmol) in N,N-dimethylformamide (200 mL) was stirred with imidazole (4.80 g, 70.6 mmol) and tert-butylchlorodimethylsilane (7.70 g, 51.0 mmol) at room temperature for one day. 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 sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=25/1→4/1 (v/v)) to give the title compound as a colorless oil (8.68 g, yield 73%).

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washthe organic layer was washed with saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=25/1→4/1 (v/v))

Sources & evidence

ORD record
ord-340dcc6da55340cf868b1649c8a47626
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

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