Sodium hydride → Benzyl 4-(1-(1-(tert-butoxycarbonyl)pyrrolidin-3-yl)-4-(4-fluoro-3-(trifluoromethyl)phenyl)-1H-imidazol-2-yl)piperidine-1-carboxylate

Participants

Reaction Steps

To a solution of 4-[4-(4-Fluoro-3-trifluoromethyl-phenyl)-1H-imidazol-2-yl]-piperidine-1-carboxylic acid benzyl ester (1000.00 mg; 2.24 mmol; 1.00 eq.) in DMF 8 ml added NaH (107.27 mg; 2.68 mmol; 1.20 eq.), stirred at RT for 20 mins, added 3-methanesulfonyloxy-pyrrolidine-1-carboxylic acid tert-butyl ester (1186.02 mg; 4.47 mmol; 2.00 eq.), the reaction mixture was stirred 85° C. for 5 hr, lc-ms showed around 40% desired, continued stirring for over night, no big changed, purified the product by HPLC (basic) with 30-100% acetonitrile/water, collected title compound 220 mg, yield 16%.

Provenance & Evidence