Imidazole → Tert-butyl 2-(2-(tert-butyldimethylsilyloxy)-1-(4-cyanophenyl)ethylamino)acetate

Participants

Reaction Steps

t-Butyldimethyl silyl chloride (0.579 g; 3.84 mmol) and imidazole (0.261 g; 3.83 mmol) were added to a solution of tert-butyl 2-(1-(4-cyanophenyl)-2-hydroxyethylamino)acetate (0.709 g; 2.56 mmol) in DMF (10 mL). The reaction mixture was stirred at ambient temperature for 18 hours. The mixture was diluted with EtOAc and washed sequentially with water and brine. The organic phase was poured through a hydrophobic frit and the solvent evaporated in vacuo. The residue was purified by flash chromatography eluting with iso-hexane/EtOAc (10:1) to afford the title compound. 1H NMR (CDCl3, 400 MHz) δ 7.63-7.61 (m, 2H), 7.48 (d, J=8.4 Hz, 2H), 3.86-3.83 (m, 1H), 3.66-3.55 (m, 2H), 3.23 (d, J=16.8 Hz, 1H), 3.06 (d, J=16.8 Hz, 1H), 2.53 (br s, 1H), 1.47 (s, 9H), 0.90 (s, 9H), 0.10 (s, 3H), 0.09 (s, 3H).

Provenance & Evidence