Imidazole → (2-Aminoethoxy)(tert-butyl)dimethylsilane

HRID 39288Notes

Reaction equation

HRID 39288 reaction equation
N1[CH:5]=[CH:4][N:3]=C1.[CH3:6][C:7]([Si:10](Cl)([CH3:12])[CH3:11])([CH3:9])[CH3:8].[OH2:14]>C(Cl)Cl>[C:7]([Si:10]([CH3:12])([CH3:11])[O:14][CH2:5][CH2:4][NH2:3])([CH3:9])([CH3:8])[CH3:6]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 529218(2-Aminoethoxy)(tert-butyl)dimethylsilaneYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.97 mL (32.74 mmol) of 156 and 2.455 g (36.06 mmol) of imidazole were dissolved in 15 mL of CH2Cl2 and 5.18 g (34.37 mmol) of TBSCl was carefully added. After 1 h at room temperature, the mixture was concentrated and loaded on a silica gel flash chromatographic column. Elution with a mixture of 20:1 (v/v) CH2Cl2/methanol containing 0.5% (by volume) triethylamine failed to afford pure product. The eluted mixture was dissolved in water, extracted with diethyl ether (3×) and dried over sodium sulfate. Removal of the solvent yielded 1.73 g (30%) of 157 as a brown oil. 1H NMR (400 MHz, CDCl3) δ 0.06 (s, 6H), 0.90 (s, 9H), 1.74 (br s, 2H), 2.77 (t, J=5.1, 2H), 3.63 (t, J=5.2, 2H).

Workup

  1. concentrationthe mixture was concentrated
  2. washElution
  3. additionwith a mixture of 20:1 (v/v) CH2Cl2/methanol containing 0.5% (by volume) triethylamine
  4. customto afford pure product
  5. extractionextracted with diethyl ether (3×)
  6. dry with materialdried over sodium sulfate
  7. customRemoval of the solvent

Sources & evidence

ORD record
ord-be8808b87b9b40e1800664fa6e9b19ae
Source dataset
uspto-grants-2013_09
Patent number
US08524691B2

Reaction notes

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