反应详情

Caesium carbonate (4.0 g, 12.4 mmol), R-BINAP (330 mg, 0.53 mmol), palladium acetate (119 mg, 0.53 mmol) and benzophenone imine (2.2 mL, 13.2 mmol) were added sequentially, each in one portion, to a stirred solution of trans-ethyl 2-[4-(4-{[(trifluoromethyl)-sulfonyl]oxy}phenyl)cyclohexyl]propanoate in THF (50 mL) and the reaction mixture was heated at 65° C. for 70 h under an argon atmosphere. The reaction mixture was cooled to room temperature and concentrated in vacuo to leave a residue. The residue was taken up in EtOAc (75 mL) and H2O (25 mL) was added. The layers were separated and the organic layer was extracted with brine (25 mL), dried and concentrated in vacuo to leave a residue. The residue was purified by chromatography, eluting with 10-50% EtOAc in isohexane, to give the title compound (2.3 g, 59%) as an oil; 1H NMR δ (CDCl3) 1.07-1.25 (2H, m), 1.15 (3H, d), 1.3 (3H, t), 1.35-1.5 (2H, m), 1.55-1.7 (2H, m), 1.72-1.8 (1H, m), 1.83-1.95 (2H, m), 2.24-2.43 (2H, m), 4.15 (2H, q), 6.7 (2H, d), 7.0 (2H, d), 7.15 (2H, d), 7.23-7.35 (1H, m), 7.4 (2H, dd), 7.47-7.55 (2H, m), 7.78 (2H, d), 7.84 (1H, d); MS m/e MH+ 440.

1. concentrationconcentrated in vacuo
2. customto leave a residue
3. customThe layers were separated
4. extractionthe organic layer was extracted with brine (25 mL)
5. customdried
6. concentrationconcentrated in vacuo
7. customto leave a residue
8. customThe residue was purified by chromatography
9. washeluting with 10-50% EtOAc in isohexane