tert-butyl 4-(4,5-dibromo-1-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)-1H-imidazol-2-yl)piperidine-1-carboxylate → tert-Butyl 4-(4-bromo-1-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)-1H-imidazol-2-yl)piperidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

Add 4-{4,5-dibromo-1-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-1H-imidazol-2-yl}-piperidine-1-carboxylic acid tert-butyl ester (39.0 g; 0.073 mol; 1.0 equiv) to THF (600 mL) and cool to −78° C. under an argon atmosphere. Add n-BuLi solution (1.6 M in cyclohexane) (53.7 mL; 0.087 mol; 1.2 equiv) drop-wise in 1 h and allow to come to −30° C. in 2 h. Quench the reaction with saturated ammonium chloride solution and extract with EA. Evaporate the organic layer and purify the residue with silica gel chromatography to give the title compound (13.2 g; 39%).

Provenance & Evidence