2-(tert-butyldiMethylsilyloxy)ethanaMine

141-43-5

18162-48-6

101711-55-1

The general procedure for the synthesis of 2-((tert-butyldimethylsilyloxy)ethylamine from 2-aminoethanol and tert-butyldimethylsilyl chloride was as follows: a solution of tert-butyldimethylsilyl chloride (3.6 g, 24 mmol) dissolved in dichloromethane (10 mL) was added slowly and dropwise over a period of 3 minutes to a stirring mixture of 2-aminoethanol (1.22 g, 20 mmol) and imidazole (2.04 g, 30 mmol) in a mixed solution. The reaction mixture was continued to be stirred at room temperature for 1 hour. Subsequently, water (20 mL) was added for quenching and the organic and aqueous phases were separated. The aqueous phase was extracted with dichloromethane (2 x 20 mL), all organic phases were combined, dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give the light yellow oily product 2-((tert-butyldimethylsilyloxy)ethylamine (3.50 g, 100% yield). The product was confirmed by NMR hydrogen spectrum (400 MHz, CDCl3): δ 3.64 (t, J = 5.0 Hz, 2H), 3.05 (br s, 2H), 2.80 (t, J = 5.0 Hz, 2H), 0.90 (s, 9H), 0.06 (s, 6H); NMR carbon spectrum (100 MHz, CDCl3): δ 64.7, 44.1, 25.9, 18.3, -3.4; mass spectrum (APCI+) showing the molecular ion peak [M + H]+ = 176.6.