Sodium hydride → HCID 86704606, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one (614 mg, 1.961 mmol) in THF (20 mL) was cooled to 0° C. NaH (58.8 mg, 2.451 mmol) was added. The mixture was stirred at 0° C. for 30 min. The title compound from Step E (462 mg, 1.63 mmol) in THF (30 mL) was added. The mixture was stirred at 0° C. and then room temperature for 4 h. Saturated NH4Cl (10 mL) was added. The mixture was extracted with ethyl acetate (3×10 mL). The combined organic fractions were washed with brine (saturated, 10 mL), dried (Na2SO4), filtered and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel Biotage 40S, eluting with EtOAc/hexane (30/70) to give the title compound as a colorless solid. 1H NMR (CDCl3, 500 MHz) δ 7.94 (s, 1H), 7.82 (s, 2H), 5.85 (d, J=8.5 Hz, 1H), 5.00 (d, J=17.5 Hz, 1H), 4.46 (m, 1H), 4.31 (d, J=18.0 Hz, 1H), 2.60 (s, 6H), 0.83 (d, J=7.0 Hz, 3H).

Provenance & Evidence