反应详情

温度

70 °C

Palladium(II) acetate (0.109 g, 0.486 mmol), DPPF (0.269 g, 0.486 mmol), K2CO3 (2.013 g, 14.57 mmol) and Et3N (0.677 mL, 4.86 mmol) were added to a solution of (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[2-iodo-5-(trifluoromethyl)benzyl]-4-methyl-1,3-oxazolidin-2-one (2.9 g, 4.86 mmol) in MeCN (30 mL) and MeOH (10 mL). The reaction mixture was purged with N2, the flask was capped and a CO balloon was attached to it. After bubbling CO gas into the solution through a needle attached to the balloon for 5 min, the mixture was heated under a CO balloon at 70° C. overnight. The mixture was diluted with EtOAc (300 mL), filtered through the Celite, then washed with water (3×50 mL), brine (1×), dried (Na2SO4), filtered and the solvent was evaporated in vacuo. The residue was purified by flash chromatography on silica gel to give methyl 2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-4-(trifluoromethyl)benzoate. LCMS calc.=530.1; found=529.9 (M+1)+. 1H NMR (500 MHz, CDCl3) δ 8.09 (d, J=8.1 Hz, 1 H); 7.92 (s, 1 H); 7.82 (s, 2 H); 7.79 (s, 1 H); 7.69 (d, J=8.1 Hz, 1 H); 5.75 (d, J=7.8 Hz, 1 H); 5.10 (d, J=16.2 Hz, 1 H); 4.81 (d, J=16.2 Hz, 1 H); 4.19-4.11 (m, 1 H); 3.99 (s, 3 H); 0.81 (d, J=6.5 Hz, 3 H).

1. customThe reaction mixture was purged with N2
2. customthe flask was capped
3. customAfter bubbling CO gas into the solution through a needle
4. additionThe mixture was diluted with EtOAc (300 mL)
5. filtrationfiltered through the Celite
6. washwashed with water (3×50 mL), brine (1×)
7. dry with materialdried (Na2SO4)
8. filtrationfiltered
9. customthe solvent was evaporated in vacuo
10. customThe residue was purified by flash chromatography on silica gel