Allyl iodide → HCID 68283865, compound

Participants

Reaction Steps

To a solution of NaH (60% in mineral oil, 8.6 mg, 0.215 mmol) in DMF (5 mL) cooled with an ice-bath and under argon was added (2S,3S,4S)-2-(3-chloro-2-fluoro-benzylcarbamoyl)-4-fluoro-3-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester (70 mg, 0.179 mmol). The reaction mixture was stirred for 20 min before addition of allyl iodide (0.025 mL, 0.269 mmol) at 0° C. The reaction mixture was stirred for 30 min then quenched by addition of water and extracted with EtOAc (×2). The organic extracts were combined, washed with brine, dried (Na2SO4), filtered and concentrated. The crude residue was purified by flash column chromatography on silica gel (c-hexane/EtOAc 3:2). MS (UPLC): 431.4/433.1 [M+H]+, 475.5/577.5 [M+HCOO]−; tR (HPLC conditions f): 2.29 min.

Provenance & Evidence