Imidazole → 3-{[tert-butyl(diphenyl)silyl]oxy}-N-(2-nitrobenzyl) propan-1-amine

Participants

Reaction Conditions

Reaction Steps

A solution of 3-[(2-nitrobenzyl)amino]propan-1-ol (1.1 g, 5.0 mmol) in dichloromethane (50 mL) was treated with imidazole (0.68 g, 10 mmol) and tert-butylchlorodiphenylsilane (1.4 mL, 5.5 mmol) and stirred at 23° C. for 2 hours. The reaction mixture was quenched by the addition of H2O (50 mL) and 2 M aqueous NaOH (10 mL), and extracted with dichloromethane (2×50 mL), dried (Na2SO4), and evaporated. Flash chromatography (SiO2, 5-50% ethyl acetate/hexanes) provided 3-{[tert-butyl(diphenyl)silyl]oxy}-N-(2-nitrobenzyl) propan-1-amine (1.8 g, 80%) as a yellow oil:

Provenance & Evidence