Allyl iodide → (S)-4-benzyl-3-((R)-2-(4-fluoro-3-methylphenoxy)pent-4-enoyl)oxazolidin-2-one

Participants

Reaction Conditions

Reaction Steps

To the solution of lithium bis(trimethylsilyl)amide (5.2 mL, 5.2 mmol, 1M in THF) in anhydrous 30 mL THF at −70° C. was slowly added over 15 minutes (S)-4-Benzyl-3-(2-(4-fluoro-3-methylphenoxy)acetyl)oxazolidin-2-one (1.5 g, 4.3 mmol) as a solution in 8.0 mL THF. The reaction mixture was stirred for 30 min at −70° C. and then was slowly added a pre-cooled solution of allyl iodide (2.2 g, 13 mmol) in 8 mL of THF. The resulting mixture was stirred at −70° C. for 1 h and the temperature was slowly raised over a period of 2 h. The mixture was poured into 60 mL saturated NH4Cl and extracted with ethyl acetate (3×40 mL). The combined organic layers were washed with brine (2×30 mL) and dried over Na2SO4. The solvent was removed under reduced pressure and the product isolated by Flash column chromatography eluting with 0% to 50% ethyl acetate/hexane to give 521 mg of the title compound as a light yellow oil.

Provenance & Evidence