Triphenylphosphine → 2-[(SR)-1-[(3RS,4SR)-1-Benzyl-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-2-(tert-butyldimethyl-silanyloxy)-ethoxy]-5-chloro-pyridine

Participants

Reaction Conditions

Reaction Steps

(SR)-1-[(3SR,4RS)-1-Benzyl-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-2-(tert-butyl-dimethyl-silanyloxy)-ethanol (described herein above) (13.2 mg. 0.0275 mmol) and PPh3 (PPh3 polymer bound, 3 mmol PPh3/g resin) (18 mg, 0.055 mmol) were suspended in THF (2 mL). To the mixture were added 5-chloro-pyridin-2-ol (7 mg, 0.055 mmol) and then DBAD (13 mg, 0.055 mmol). The reaction mixture was stirred at 40° C. over night. The mixture was diluted with ethyl acetate and filtered on celite and concentrated under vacuo. The residue was purified by TLC (SiO2, EtOAc/H, 1:4) yielded 7.2 mg (44%) of the title compound as a colorless oil. ES-MS m/e: 593.3 (M+H+).

Provenance & Evidence