Sodium hydride → HCID 67265095, compound

Participants

Reaction Conditions

Reaction Steps

In a dry round bottom flask, charge 4-[4-(4-fluoro-3-trifluoromethyl-phenyl)-1H-imidazol-2-yl]-piperidine-1-carboxylic acid tert-butyl ester (1.5 g; 0.0036 mol; 1.0 equiv) in dry DMF (30 mL) and cool to 0° C. Add NaH (0.26 g; 0.011 mol; 3.0 equiv) in portions under nitrogen and stir at RT for 30 min. Add 2-(toluene-4-sulfonyloxymethyl)-pyrrolidine-1-carboxylic acid benzyl ester (2.46 g; 0.0072 mol; 2.0 equiv) at RT and heat at 40° C. overnight. Quench with cold water and extract in EA. Wash the organic layer with water and brine. Dry over anhydrous sodium sulfate and concentrate. Purify the crude residue on silica (100-200 mesh) with 10 to 20% EA/hexanes to give the title compound (1.14 g; 51.6%). (ES+): m/z=631 (M+H).

Provenance & Evidence