Triphenylphosphine → (5R)-3-[4-(3,6-dihydro-2H-pyran-4-yl)-3-fluoro-phenyl]-5-(isoxazol-3-yloxymethyl)oxazolidin-2-one

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Reaction Steps

Diisopropylazodicarboxylate (248 mg, 1.22 mmol) was added dropwise, at ambient temperature, to a stirred solution of 5(R)-hydroxymethyl-3-(3-fluoro-4-(3,6-dihydro-(2H)-pyran-4-yl)phenyl)oxazolidin-2-one (International Patent Application Publication WO 97/09328) (300 mg, 1.02 mmol), 3-hydroxyisoxazole (104 mg, 1.22 mmol) and triphenylphosphine (340 mg, 1.30 mmol) in THF (8.0 ml). The resulting solution was stirred at ambient temperature for 30 minutes before evaporating the solvent to give an oil which was purified by flash chromatography (Merck 9385 silica, EtOAc/iso-hexane (7:3) eluant) to give the title product (219 mg, 59%) as a crystalline solid.

Provenance & Evidence