Imidazole → Benzyl({2-[(tert-butyldimethylsilyl)oxy]ethyl})amine

HRID 1977660Notes

Reaction equation

HRID 1977660 reaction equation
CN(C)C=[O:4].[CH2:6](CC(N)O)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[Si:17](Cl)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18].N1[CH:29]=[CH:28][N:27]=C1>O>[CH2:6]([NH:27][CH2:28][CH2:29][O:4][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chlorideHCID 183803092-Benzyl-aminoethanol

Product 1

HCID 21993563Benzyl({2-[(tert-butyldimethylsilyl)oxy]ethyl})amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

An N,N-dimethylformamide (40 ml) solution of 2-benzyl-aminoethanol (3 g), tert-butyldimethylsilyl chloride (3.6 g), and imidazole (3.4 g) was stirred at room temperature for 1 hour in a stream of argon air. Water (300 ml) was added to the reaction solution, and the solution was extracted with ethyl acetate. The organic phase was washed with water and saturated brine, dried over sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was dried to obtain the desired compound (5.3 g, quantitative) as a pale yellow oil.

Workup

  1. extractionthe solution was extracted with ethyl acetate
  2. washThe organic phase was washed with water and saturated brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe resulting residue was dried

Sources & evidence

ORD record
ord-bdb7e3eb936c453ca39016c012005e8d
Source dataset
uspto-grants-2001_05
Patent number
US06235730B1

Reaction notes

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