Sodium hydride → HCID 67016478, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of [(3RS,4RS)-1-benzyl-4-(4-chloro-phenyl)-3-methyl-pyrrolidin-3-yl]-methanol (4.0 g, 12.7 mmol) in DMF (60 mL) at RT was added NaH (608 mg, 60%, 15.2 mmol). The reaction mixture was heated at 50° C. for 30 minutes, then cooled down to RT before 2-bromo-5-chloropyridine (3.66 g, 19.0 mmol) was added. The resulting brownish solution was stirred overnight at 60° C., then concentrated under high vacuum. The residues was taken up in EtOAc, and washed with water. The organic phase was dried over Na2SO4 and a purification by column chromatography gave 3.90 g (72%) of the title product as a viscous oil. ES-MS m/e: 427.2 (M+H+).

Provenance & Evidence