Potassium Iodide → Bisegliptin

Participants

Reaction Steps

Ethyl 4-aminobicyclo[2.2.2]octane-1-carboxylate hydrochloride (206 mg), potassium carbonate (243.2 mg), potassium iodide (13.3 mg) and N,N-dimethylformamide (5 mL) were mixed together. To this mixture, a solution of (2S,4S)-4-fluoro-1-[2-(benzenesulfonyloxy)acetyl]pyrrolidine-2-carbonitrile (250 mg) in N,N-dimethylformamide (1.5 mL) was added at 50° C. and the mixture was further stirred for 1 hour. Subsequently, the reaction mixture was concentrated under reduced pressure and the residue was purified on a silica gel column (eluant=ethyl acetate:methanol=20:1) to give (2S,4S)-1-[2-[(4-ethoxycarbonylbicyclo[2.2.2]oct-1-yl)amino]ac etyl]-4-fluoropyrrolidine-2-carbonitrile as a white solid (260 mg, 92% yield).

Provenance & Evidence