Sodium hydride → HCID 66853057, compound

HRID 1162318Notes

Reaction equation

HRID 1162318 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH2:22][C:23]2[N:24]=[CH:25][NH:26][CH:27]=2)[C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:30][Si:31]([CH3:38])([CH3:37])[CH2:32][CH2:33][O:34][CH2:35]Cl>CN(C=O)C.C(OCC)(=O)C.O>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH2:22][C:23]2[N:24]=[CH:25][N:26]([CH2:35][O:34][CH2:33][CH2:32][Si:31]([CH3:38])([CH3:37])[CH3:30])[CH:27]=2)[C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 178453108HCID 178453108, compound

Product 1

HCID 66853057HCID 66853057, compoundYield 24%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl (1-benzyl-4-piperidinyl)((1H-imidazol-4-yl)methyl)carbamate (1.3 g) obtained in Example 83b) in DMF (30 ml) was added sodium hydride (0.22 g) under ice-cooling, and mixed at room temperature for 1 hour. Subsequently, 2-(trimethylsilyl)ethoxymethyl chloride (1.3 ml) was added under ice-cooling, and then mixed at room temperature for 2 hours. The reaction solution was diluted with ethyl acetate and water, and the organic layer was collected by separation. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified with basic silica gel column (ethyl acetate:hexane=1:1) to obtain the title compound as a pale yellow oil (4.9 g, 24%).

Workup

  1. temperaturecooling
  2. additionmixed at room temperature for 1 hour
  3. temperaturecooling
  4. additionmixed at room temperature for 2 hours
  5. customthe organic layer was collected by separation
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe residue was purified with basic silica gel column (ethyl acetate:hexane=1:1)

Sources & evidence

ORD record
ord-4d457d30aa664d24af446df09f8b7832
Source dataset
uspto-grants-2010_10
Patent number
US07820673B2

Reaction notes

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