Water → HCID 59383142, compound

Participants

Reaction Steps

(2S,4S)-1-[[N-(4-Carboxybicyclo[2.2.2]oct-1-yl)amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile (30.0 mg) was dissolved in N,N-dimethylformamide (1.0 mL) and cesium carbonate (45.3 mg) was added to the solution. Benzyl bromide (17.5 mg) in N,N-dimethylformamide (0.5 mL) was then added while the mixture was chilled in an ice bath and the mixture was stirred for 1 hour. Subsequently, water was added and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluant:dichloromethane:methanol=10:1) to give (2S,4S)-1-[[N-(4-benzyloxycarbonyl bicyclo[2.2.2]oct-1-yl)amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile (30.6 mg).

Provenance & Evidence