Imidazole → HCID 89714623, compound

HRID 2273070Notes

Reaction equation

HRID 2273070 reaction equation
[NH2:1][CH2:2][C:3]([CH3:7])([CH3:6])[CH2:4][OH:5].N1C=CN=C1.[C:13]([Si:17](Cl)([CH3:19])[CH3:18])([CH3:16])([CH3:15])[CH3:14]>C(Cl)Cl>[Si:17]([O:5][CH2:4][C:3]([CH3:7])([CH3:6])[CH2:2][NH2:1])([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 1173261-Propanol, 3-amino-2,2-dimethyl-

Product 1

HCID 89714623HCID 89714623, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2 g of 3-amino2,2-dimethylpropan-1-ol (19.39 mmol) are placed in 40 ml of DCM. 2.56 g of imidazole (38.77 mmol) are added and the solution is cooled to +4° C. in an ice bath, followed by dropwise addition of 3.36 ml of tert-butyl(chloro)dimethylsilane (19.39 mmol). The medium is stirred for 30 minutes at +4° C., and the ice bath is then removed and the mixture is stirred at room temperature for 18 hours. The medium is then washed with water, and then with brine. The organic phase is dried over Na2SO4, filtered and concentrated to give 4.02 g of 3-(tert-butyldimethylsilanyloxy)-2,2-dimethylpropylamine.

Workup

  1. temperaturethe solution is cooled to +4° C. in an ice bath
  2. customthe ice bath is then removed
  3. stirringthe mixture is stirred at room temperature for 18 hours
  4. washThe medium is then washed with water
  5. dry with materialThe organic phase is dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4e0243a846d5406ca07df81797b45b75
Source dataset
uspto-grants-2015_09
Patent number
US09120812B2

Reaction notes

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