Imidazole → (3-Aminopropoxy)(tert-butyl)dimethylsilane

HRID 595507Notes

Reaction equation

HRID 595507 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][OH:5].N1C=CN=C1.[C:11]([Si:15](Cl)([CH3:17])[CH3:16])([CH3:14])([CH3:13])[CH3:12]>C(Cl)Cl>[Si:15]([O:5][CH2:4][CH2:3][CH2:2][NH2:1])([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 90863-Amino-1-propanolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 11074190(3-Aminopropoxy)(tert-butyl)dimethylsilane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 3-aminopropan-1-ol (2 g, 20 mmol) in DCM (10 mL), imidazole (79 mmol, 3 equiv.) was added and stirred at room temperature for 10 min. Reaction mixture was cooled to 0° C., t-butyl dimethyl silyl chloride (30 mmol, 1.2 equiv.) was added in portions and stirred the reaction mixture overnight at room temperature. Diluted the reaction mixture using DCM, the DCM layer was washed with water. The organic layer was collected, dried over Na2SO4, filtered and concentrated. ELSD method LC/MS: Retention time: 1.5 min; (ES-API), m/z 189.7 (M+H).

Workup

  1. customReaction mixture
  2. temperaturewas cooled to 0° C.
  3. stirringstirred the reaction mixture overnight at room temperature
  4. additionDiluted the reaction mixture
  5. washthe DCM layer was washed with water
  6. customThe organic layer was collected
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-12c14708cab84c069d1bc5af6d4372f8
Source dataset
uspto-grants-2016_01
Patent number
US09242976B2

Reaction notes

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