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

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Reaction Steps

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%).

Provenance & Evidence