Tetrahydrofuran → (2S,4S)-1-[[N-benzyloxycarbonyl-N-[4-(piperidin-1-yl)carbonylbicyclo[2.2.2]oct-1-yl]amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile

Participants

Reaction Steps

(2S,4S)-1-[[N-Benzyloxycarbonyl-N-[4-(benzotriazol-1-yl)oxycarbonylbicyclo[2.2.2]oct-1-yl]amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile (20.0 mg) and pyrrolidine (4.4 μL) were dissolved in tetrahydrofuran (0.4 mL) and the mixture was stirred at room temperature for 25 minutes. The solvent was removed under reduced pressure and the residue was dissolved in dichloromethane. The organic layer washed sequentially with 0.1 N aqueous hydrochloric acid, saturated aqueous sodium bicarbonate solution and saturated brine. The organic layer was then dried over anhydrous sodium sulfate and was concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (eluant:ethyl acetate:methanol=20:1) to give (2S,4S)-1-[[N-benzyloxycarbonyl-N-[4-(piperidin-1-yl)carbonylbicyclo[2.2.2]oct-1-yl]amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile (16.0 mg).

Provenance & Evidence