Triphenylphosphine → 2-[(R)-1-[(3R,4S)-1-Benzyl-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-5-chloro-pyridine

Participants

Reaction Conditions

Reaction Steps

(S)-1-[(3R,4S)-1-Benzyl-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-2-(tert-butyl-dimethyl-silanyloxy)-ethanol (17) and PPh3 (PPh3 polymer bound, 3 mmol PPh3/g resin) (614 mg, 1.87 mmol) were suspended in THF (10 mL). To the mixture were added 5-chloro-pyridin-2-ol (0.243 g, 1.87 mmol) and then DBAD (0.431 g, 1.87 mmol). The reaction mixture was stirred at 45° C. over night. The mixture was diluted with ethyl acetate and filtered on celite and concentrated under vacuo. The residue was purified by column chromatography (SiO2, EtOAc/H, 1:15) yielded 571 mg (77%) of the title compound as a colorless oil. ES-MS m/e: 593.3 (M+H+).

Provenance & Evidence