反应详情

To a degassed solution of the title compound from Example 136 Step A (3.17 g, 9.99 mmol) in EtOAc (50 mL) was added platinum oxide (0.68 g, 3.00 mmol). The reaction flask was fitted with a hydrogen balloon attached to a 3-way adapter. The reaction mixture was then evacuated and back-filled with hydrogen. After this process was repeated three times, the reaction mixture was placed under a hydrogen atmosphere, and was stirred vigorously. After 45 min, the reaction mixture was filtered though Celite, rinsing with EtOAc. The mixture was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. Purification by chromatography on silica gel (0 to 8% EtOAc in hexanes, 8% EtOAc in hexanes, then 8 to 100% EtOAc in hexanes) provided the title compound: LCMS m/z 264.0 [M-t-Boc]+; 1H NMR (500 MHz, CDCl3) δ 7.99 (d, J=8.5 Hz, 2H), 7.30 (d, J=8.0 Hz, 2H), 4.37 (q, J=7.0 Hz, 2H), 3.92-3.76 (br m, 1H), 3.70-3.52 (br m, 1H), 3.48-3.34 (br m, 2H), 3.30 (t, J=10.0 Hz, 1H), 2.34-2.24 (br m, 1H), 1.99 (q, J=10.0 Hz, 1H), 1.48 (s, doubled (rotamers), 9H), 1.39 (t, J=7.0 Hz, 3H).

1. customattached to a 3-way adapter
2. customThe reaction mixture was then evacuated
3. additionback-filled with hydrogen
4. filtrationthe reaction mixture was filtered though Celite
5. washrinsing with EtOAc
6. dry with materialThe mixture was dried over anhydrous sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customPurification by chromatography on silica gel (0 to 8% EtOAc in hexanes, 8% EtOAc in hexanes