Imidazole → HCID 86722309, compound

HRID 874819Notes

Reaction equation

HRID 874819 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][CH2:7][N:8]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:9][CH2:10][OH:11].N1C=CN=C1.[Si:24](Cl)([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25]>CN(C=O)C.C(OCC)(=O)C>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][CH2:7][N:8]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:9][CH2:10][O:11][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 867223102-((2-(1,3-Dioxolan-2-yl)ethyl)(benzyl)amino)ethanol

Product 1

HCID 86722309HCID 86722309, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 2-((2-(1,3-dioxolan-2-yl)ethyl)(benzyl)amino)ethanol (2.81 g, 11.2 mmol) in DMF (10 mL) was added imidazole (1.67 g, 24.61 mmol) and tert-butyldimethylsilyl chloride (3.35 g, 22.39 mmol). The reaction mixture was stirred at RT for 18 hours. The reaction mixture was diluted with ethyl acetate and washed with water and brine. The organic phase was dried (magnesium sulfate), filtered and the solvent evaporated art reduced pressure (3.87 g, 95%).

Workup

  1. washwashed with water and brine
  2. dry with materialThe organic phase was dried (magnesium sulfate)
  3. filtrationfiltered
  4. customthe solvent evaporated art reduced pressure (3.87 g, 95%)

Sources & evidence

ORD record
ord-28f859f0ed8341edac3977e3ebd8f9c7
Source dataset
uspto-grants-2015_03
Patent number
US08980913B2

Reaction notes

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