Imidazole → 2-(tert-butyldiphenylsilyloxy)-N-methylethanamine

HRID 17387

Reaction equation

HRID 17387 reaction equation
[C:1]([Si:5](Cl)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:19][NH:20][CH2:21][CH2:22][OH:23].N1C=CN=C1>CN(C)C=O>[O:23]([CH2:22][CH2:21][NH:20][CH3:19])[Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 80162-(Methylamino)ethanolHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 118231582-(tert-butyldiphenylsilyloxy)-N-methylethanamineYield 39%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Under nitrogen atmosphere, an N,N-dimethylformamide (33 ml) solution of tert-butylchlorodiphenylsilane (8.78 g, 32.0 mmol) was dropwise added at room temperature to an N,N-dimethylformamide (100 ml) solution of N-methylethanolamine (2.00 g, 26.6 mmol) and imidazole (2.72 g, 39.9 mmol), and stirred for 5.5 hours. The solvent was evaporated away under reduced pressure, then the residue was dissolved in ethyl acetate, and the solution was washed with saturated sodium hydrogencarbonate water, water and saturated brine. Next, the organic layer was dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography, and the eluate with ethyl acetate gave the entitled compound (3.21 g, 39%) as a pale yellow oil.

Workup

  1. customThe solvent was evaporated away under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washthe solution was washed with saturated sodium hydrogencarbonate water, water and saturated brine
  4. dry with materialNext, the organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7114c87529a548ad8d6885f843c342be
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Linked notes

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