Sodium hydride → HCID 67131413, compound

Participants

Reaction Steps

To a stirred solution of 88 mg (0.26 mmol) of (S)-1-[(3R,4S)-1-benzyl-4-(4-chloro-3-fluoro-phenyl)-pyrrolidin-3-yl]-ethanol in DMF (6 mL) was added NaH (19 mg, 0.40 mmol). The reaction mixture was stirred at RT for 30 minutes, and then at 50° C. for 20 minutes. A solution of 6-chloro-nicotinonitrile (45 mg, 0.32 mmol) in DMF (2 mL) was added dropwise and stirring was continued 3 hours at 50° C. The reaction mixture was concentrated under vacuo. Extraction with EtOAc/H2O, followed by column chromatography (SiO2, EtOAc/H, 1:3) yielded 100 mg (87%) of the title compound as a colorless oil. ES-MS m/e: 436.2 (M+H+).

Provenance & Evidence