Isopropanol → 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 tert-butyl 4-(4,5-dibromo-1-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)-1H-imidazol-2-yl)piperidine-1-carboxylate (46.00 g 85.61 mmol) in tetrahydrofuran (1 L). Cool to −78° C. under nitrogen. Add 1.6 M butyllithium in hexanes (90.97 mL, 1.7 eq) dropwise over 15 minutes. Maintain the internal temperature below −65° C. After 65 minutes, add isopropyl alcohol (50 mL). Allow to warm to room temperature over 2 hr. Dilute with saturated aqueous ammonium chloride, then extract with ethyl acetate three times. Wash the organics with saturated aqueous sodium chloride. Dry over anhydrous magnesium sulfate, filter, and concentrate in vacuo to give the title compound (43.00 g, 100%). MS (ES) m/z=460 [M]+.

Provenance & Evidence