Triphenylphosphine → HCID 67033452, compound

Participants

Reaction Steps

To a suspension of PPh3 (PPh3 polymer bound, 3 mmol PPh3/g resin) (0.914 g, 2.74 mmol) in THF (15 mL) at 0° C. were added 5-fluoro-pyridin-2-ol (0.215 g, 1.90 mmol) and then DBAD (0.47 g, 2.02 mmol). After 5 minutes was added (R)-1-[(3R,4S)-1-benzyl-4-(4-chloro-phenyl)-pyrrolidin-3-yl]-ethanol (0.40 g, 1.26 mmol; described herein above). The reaction mixture was stirred over night at RT, filtered on celite and concentrated under vacuo. Extraction with EtOAc/aq.NaOH 1M, followed by column chromatography (SiO2, EtOAc/H, 1:3) yielded 0.315 g (44%) of the title compound as a colorless oil. ES-MS m/e: 411.2 (M+H+).

Provenance & Evidence