Imidazole → 2-tert-Butyldimethylsilyloxy-1,1-dimethylethylamine

Participants

Reaction Steps

To a stirred solution of 2-amino-2-methylpropan-1-ol (1.78 g, 0.02 mol) in dichloromethane (25 mL) was added tert-butyldimethylsilyl chloride (5.4 g, 0.036 mol) followed by imidazole (3.4 g, 0.05 mol). The mixture was stirred at room temperature for 16 hours. The solvent was removed under reduced pressure. The residue was diluted with water and extracted with EtOAc (3×30 mL). The combined organic layers were washed with NaHCO3 aqueous, brine and dried over Na2SO4. After filtration and concentration, the residue was purified by column chromatography on silica gel eluting with EtOAc to give 1-(tert-butyldimethylsilyloxy)-2-methylpropan-2-amine (3.1 g, 76%) as an oil. 1H NMR (300 MHz, CDCl3): δ 3.26 (s, 2H), 1.02 (s, 6H), 0.88 (s, 9H), 0.03 (s, 6H).

Provenance & Evidence