反应详情

温度

25 °C

A solution of 86 (0.043 g, 0.095 mmol, 1 equiv) in THF (1.5 mL) was treated with 10% Pd—C (0.020 g, 0.019 mmol, 0.2 equiv) followed by aqueous HCO2NH4 (0.5 mL, 25% w/v, 1.98 mmol, 21 equiv) and the resulting black suspension was stirred rapidly at 25° C. for 2.5 h. The crude mixture was filtered through a plug of Celite to afford a biphasic filtrate which was partitioned. The aqueous portion was extracted with EtOAc (2×1 mL) and the combined organic portions were dried (MgSO4), filtered, and concentrated to provide 87 as an analytically pure white solid (0.032 g, 0.034 g theoretical, 94%). Recrystallization from 10% EtOAc-hexane gave colorless plates suitable for X-ray analysis:24 mp 157-159° C.; 1H NMR (400 MHz, CDCl3) major rotamer δ 7.98-7.94 (m, 1H), 7.37-7.32 (m, 1H), 7.22-7.19 (m, 1H), 6.96-6.90 (m, 1H), 6.47 (s, 1H), 4.41-4.26 (m, 1H), 4.19-4.07 (m, 1H), 3.89-3.81 (m, 2H), 2.88-2.78 (m, 1H), 2.51-2.46 (m, 1H), 2.18-2.05 (m, 1H), 1.71-1.67 (m. 2H), 1.40 (s, 9H); 1H NMR 400 MHz, acetone-d6) major rotamer δ 9.17 (s, 1H), 8.27 (d, J=8.1 Hz, 1H), 8.19-8.17 (m, 1H), 7.59-7.54 (m, 1H), 7.50-7.46 (m, 1H), 6.75 (s, 1H), 4.39-4.36 (m, 1H), 4.19-4.15 (m, 1H), 3.92-3.87 (m, 1H), 3.75-3.63 (m, 1H), 2.75-2.68 (m, 1H), 2.37-2.33 (m, 1H), 2.06-2.04 (m, 1H), 1.69-1.67 (m, 2H), 1.40 (s, 9H); 13C NMR(100 MHz, CDCl3)major rotamer δ 155.8, 152.9, 151.6, 139.3, 132.3, 126.5, 124.9, 124.7, 123.5, 122.4, 109.4, 81.5, 48.9, 44.6, 38.6, 28.4 (3C), 26.3, 24.2; IR (film) νmax 3287, 2965, 2915, 2844, 1693, 1663 cm−1; FABHRMS (NBA-NaI) m/z 384.1352 (M+Na+, C20H24CINO3 requires 384.1342).

1. filtrationThe crude mixture was filtered through a plug of Celite
2. customto afford a biphasic filtrate which
3. customwas partitioned
4. extractionThe aqueous portion was extracted with EtOAc (2×1 mL)
5. dry with materialthe combined organic portions were dried (MgSO4)
6. filtrationfiltered
7. concentrationconcentrated