Triphenylphosphine → (3RS,4SR)-1-Benzyl-3-(3,4-dichloro-phenyl)-4-[(RS)-1-(4-trifluoromethyl-phenoxy)-ethyl]-pyrrolidine

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Reaction Steps

To a suspension of PPh3 (PPh3 polymer bound, 3 mmol PPh3/g resin) (1.80 g, 5.59 mmol) in THF (40 mL) at 0° C. were added 4-trifluoromethyl-phenol(0.618 g, 3.81 mmol) and then DBAD (0.936 g, 4.07 mmol). After 5 minutes was added (SR)-1-[(3SR,4RS)-1-benzyl-4-(3,4dichloro-phenyl)-pyrrolidin-3-yl]-ethanol (X-B-1) (0.89 g, 2.54 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, 1:6) yielded 0.990 g (79%) of the title compound as a colorless oil. ES-MS m/e: 493.0 (M+H+).

Provenance & Evidence