Imidazole → HCID 23138644, compound

HRID 1171647Notes

Reaction equation

HRID 1171647 reaction equation
[CH2:1]([O:3][C:4](/[CH:6]=[C:7]1\[CH2:8][N:9]([C:14]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][CH2:11][CH:12]\1[OH:13])=[O:5])[CH3:2].[Si:33](Cl)([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:35])[CH3:34].N1C=CN=C1>CN(C)C=O.CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[Si:33]([O:13][CH:12]1[CH2:11][CH2:10][N:9]([C:14]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:8]/[C:7]/1=[CH:6]\[C:4]([O:3][CH2:1][CH3:2])=[O:5])([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:35])[CH3:34]

Participants

7

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 23000851Ethyl (2E)-[4-hydroxy-1-(triphenylmethyl)piperidin-3-ylidene]acetate

Product 1

HCID 23138644HCID 23138644, compoundYield 86.3%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (E)-3-[(ethoxycarbonyl)methylidene]-1-(triphenylmethyl)piperidin-4-ol (14.97 g) in N,N-dimethylformamide (130 ml) were added successively t-butyldimethylsilyl chloride (6.86 g), 1H-imidazole (3.34 g) and 4-dimethylaminopyridine (0.43 g) under ice-cooling, and the resulting mixture was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate and washed with saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous sodium sulfate. The solvent was removed, and the residue was purified by chromatography on a silica gel column using a mixed solvent of ethyl acetate and hexane (1:19) as the eluent to afford the title compound (16.38 g, yield: 86%) as a colourless amorphous solid.

Workup

  1. temperaturecooling
  2. washwashed with saturated aqueous sodium chloride solution
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customThe solvent was removed
  5. customthe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-0d32ef0c8dac457983f6d2fc0f1b2f2e
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

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