反应详情

温度

80 °C

4-Methoxy-benzylamine (3.40 mL, 3.59 g, 26.20 mmol) and anhydrous DMSO (5.20 mL) were added to a high-pressure flask charged with 36 (3.00 g, 9.58 mmol), K3PO4 (4.19 g, 19.73 mmol), CuII (290 mg, 1.52 mmol), and L-(−)-proline (255 mg, 2.21 mmol); the sealed flask was heated to 80° C. for 44 hours. After cooling to room temperature, reaction contents were partitioned between water (100 mL) and EtOAc (200 mL), then were extracted with EtOAc (2×200 mL). The combined organic layers were washed with saturated aqueous NaCl solution (500 mL), dried (Na2SO4), filtered, and concentrated. The residue was purified via column chromatography (SiO2, 7:1:1 Hexanes:CH2Cl2:EtOAc) to give 37 as a light orange amorphous solid (952 mg, 27%): 1H NMR (CDCl3, 500 MHz) δ 7.55 (d, J=8.7 Hz, 2H), 7.49 (m, 2H), 7.41 (m, 2H), 7.37-7.32 (m, 3H), 7.15 (dd, J=8.8, 2.6 Hz, 1H), 7.13 (m, 1H), 6.92 (dd, J=8.8, 2.3 Hz, 1H), 6.90 (d, J=8.7 Hz, 2H), 6.87 (m, 1H), 5.14 (s, 2H), 4.35 (s, 2H), 3.82 (s, 3H); 13C NMR (CDCl3, 125 MHz) δ 159.1, 154.6, 137.4, 130.7, 129.3 (2C), 128.8 (2C), 128.1, 128.0, 127.8 (2C), 119.4 (2C), 118.6, 114.3 (2C), 107.9, 70.3, 55.5; IR (film) νmax 3734, 1558, 1456, 1259, 1167, 847, 746, 702, 660 cm−1; HRMS (ESI+) m/z: [M+H]+ calcd for C25H23NO2, 370.1807. found, 370.1786.

1. temperatureAfter cooling to room temperature
2. customreaction contents
3. customwere partitioned between water (100 mL) and EtOAc (200 mL)
4. extractionwere extracted with EtOAc (2×200 mL)
5. washThe combined organic layers were washed with saturated aqueous NaCl solution (500 mL)
6. dry with materialdried (Na2SO4)
7. filtrationfiltered
8. concentrationconcentrated
9. customThe residue was purified via column chromatography (SiO2, 7:1:1 Hexanes:CH2Cl2:EtOAc)