Imidazole → (R)-1-((tert-butyldimethylsilyl)oxy)propan-2-amine

HRID 1243220Notes

Reaction equation

HRID 1243220 reaction equation
Cl.[NH2:2][C@@H:3]([CH2:5][OH:6])[CH3:4].N1C=CN=C1.[Si:12](Cl)([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]>CN(C)C=O>[C:15]([Si:12]([CH3:14])([CH3:13])[O:6][CH2:5][C@H:3]([NH2:2])[CH3:4])([CH3:18])([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 734254842-Aminopropanol hydrochloride, (R)-

Product 1

HCID 22867570(R)-1-((tert-butyldimethylsilyl)oxy)propan-2-amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

D-Alaninol hydrochloride (500 mg, 6.66 mmol) (Aldrich) was dissolved in anhydrous dimethylformamide (10 mL) (Aldrich). Imidazole (544 mg, 8 mmol) (Aldrich) and tert-butyldimethylsilyl chloride (1.05 g, 7 mmol) (Aldrich) were successively added at room temperature. This mixture was stirred at room temperature for 2 hours, quenched with a solution of water-saturated aqueous sodium bicarbonate solution (5:1, 15 mL) and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over sodium sulfate, and concentrated under reduce pressure to yield (R)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethylamine as a colorless oil. (Yield 852 mg, 68%).

Workup

  1. customquenched with a solution of water-saturated aqueous sodium bicarbonate solution (5:1, 15 mL)
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6478f67e9d5842cc9220289aba93fc9d
Source dataset
uspto-grants-2006_10
Patent number
US07115740B2

Reaction notes

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