Hydrochloric Acid → (5R)-3-{3-Fluoro-4-[3-(hydroxymethyl)isoxazol-5-yl]phenyl}-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-2-one

Participants

Reaction Steps

Ethyl 5-{2-fluoro-4-[(5R)-2-oxo-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-3-yl]phenyl}isoxazole-3-carboxylate (Example 2, 0.4 g, 1.1 mmol) was suspended in methanol/dichloromethane/dimethylsulfoxide (9 ml:3 ml:1 ml). Lithium borohydride (0.12 g, 5.5 mmol) was added portionwise. The reaction mixture was stirred under nitrogen at room temperature for 1 hour. The pH was adjusted to pH 3–4 using 1N hydrogen chloride, the mixture was cooled to 0° C., and the resulting white precipitate was collected by suction filtration. The white solid was dried in vacuo, giving 0.28 g of the desired product.

Provenance & Evidence