Methyl iodide → tert-butyl 4-methoxy-4-(1-methyl-1H-imidazol-2-yl)piperidine-1-carboxylate

HRID 1910391Notes

Reaction equation

HRID 1910391 reaction equation
[OH:1][C:2]1([C:15]2[N:16]([CH3:20])[CH:17]=[CH:18][N:19]=2)[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[H-].[Na+].[CH3:23]I>CN(C=O)C>[CH3:23][O:1][C:2]1([C:15]2[N:16]([CH3:20])[CH:17]=[CH:18][N:19]=2)[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 68570244tert-butyl 4-hydroxy-4-(1-methyl-1H-imidazol-2-yl)piperidine-1-carboxylate

Product 1

HCID 68570558tert-butyl 4-methoxy-4-(1-methyl-1H-imidazol-2-yl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl 4-hydroxy-4-(1-methyl-1H-imidazol-2-yl)piperidine-1-carboxylate (300 mg) in DMF (3 ml) was added NaH (60% dispersion in mineral oil; 77 mg) and MeI (120 μl) under ice bath cooling, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was extracted with EtOAc and was washed with water and brine, and was dried over MgSO4. Solvent was removed in vacuo, and the residue was purified by silica gel column (n-hexane:EtOAc=50:50 to EtOAc only) to give tert-butyl 4-methoxy-4-(1-methyl-1H-imidazol-2-yl)piperidine-1-carboxylate (182 mg) as a colorless oil.

Workup

  1. temperaturecooling
  2. extractionThe reaction mixture was extracted with EtOAc
  3. washwas washed with water and brine
  4. dry with materialwas dried over MgSO4
  5. customSolvent was removed in vacuo
  6. customthe residue was purified by silica gel column (n-hexane

Sources & evidence

ORD record
ord-4222368124444b94aef5b14bcca463d9
Source dataset
uspto-grants-2013_12
Patent number
US08603975B2

Reaction notes

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