Imidazole → 2-tert-Butyldimethylsilyloxy-1,1-dimethylethylamine

HRID 246602Notes

Reaction equation

HRID 246602 reaction equation
[NH2:1][C:2]([CH3:6])([CH3:5])[CH2:3][OH:4].[Si:7](Cl)([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8].N1C=CN=C1>ClCCl>[Si:7]([O:4][CH2:3][C:2]([CH3:6])([NH2:1])[CH3:5])([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 118072-Amino-2-methyl-1-propanolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 148067402-tert-Butyldimethylsilyloxy-1,1-dimethylethylamineYield 76.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-amino-2-methylpropan-1-ol (1.78 g, 0.02 mol) in dichloromethane (25 mL) was added tert-butyldimethylsilyl chloride (5.4 g, 0.036 mol) followed by imidazole (3.4 g, 0.05 mol). The mixture was stirred at room temperature for 16 hours. The solvent was removed under reduced pressure. The residue was diluted with water and extracted with EtOAc (3×30 mL). The combined organic layers were washed with NaHCO3 aqueous, brine and dried over Na2SO4. After filtration and concentration, the residue was purified by column chromatography on silica gel eluting with EtOAc to give 1-(tert-butyldimethylsilyloxy)-2-methylpropan-2-amine (3.1 g, 76%) as an oil. 1H NMR (300 MHz, CDCl3): δ 3.26 (s, 2H), 1.02 (s, 6H), 0.88 (s, 9H), 0.03 (s, 6H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionThe residue was diluted with water
  3. extractionextracted with EtOAc (3×30 mL)
  4. washThe combined organic layers were washed with NaHCO3 aqueous, brine
  5. dry with materialdried over Na2SO4
  6. filtrationAfter filtration and concentration
  7. customthe residue was purified by column chromatography on silica gel eluting with EtOAc

Sources & evidence

ORD record
ord-238f9a1fa7e3400d972124944da060ff
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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