Triphenylphosphine → HCID 67131386, compound

Participants

Reaction Steps

To a suspension of PPh3 (PPh3 polymer bound, 3 mmol PPh3/g resin) (1.78 g, 6.79 mmol) in THF (20 mL) at 0° C. were added 5-chloro-pyridin-2-ol (0.60 g, 4.63 mmol) and then DBAD (1.14 g, 4.95 mmol). After 5 minutes was added (R)-1-[(3R,4S)-1-benzyl-4-(3,4-difluoro-phenyl)-pyrrolidin-3-yl]-ethanol (0.98 g, 3.09 mmol). 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 0.917 g (69%) of the title compound as a colorless oil. ES-MS m/e: 429.2 (M+H+).

Provenance & Evidence