反应详情

温度

60 °C

A solution containing benzyl 2-(hydroxymethyl)-1-indolinecarboxylate (Preparation 6, 1.78 g), N-iodosuccinimide (2.83 g), and anhydrous DMF (12 mL) is stirred overnight at 60° C. in a foil-covered flask. This solution is cooled and concentrated to half volume with a stream of nitrogen. The resulting brown solution is partitioned between water (50 mL) and CH2Cl2 (150 mL). The organic phase is washed with brine, dried (Na2SO4), filtered, and concentrated to give a brown oil. The crude product is chromatographed eluting with 0-40% EtOAc in heptane (300 mL each 10%) to give 2.03 g (79%) of the title compound as a peach solid. Physical characteristics: M.p. 110-111° C.; HRMS (FAB) m/z 410.0270 (C17H16INO3+H). Anal. Found: C, 49.83; H, 3.95; N, 3.37.

1. temperatureThis solution is cooled
2. concentrationconcentrated to half volume with a stream of nitrogen
3. customThe resulting brown solution is partitioned between water (50 mL) and CH2Cl2 (150 mL)
4. washThe organic phase is washed with brine
5. dry with materialdried (Na2SO4)
6. filtrationfiltered
7. concentrationconcentrated
8. customto give a brown oil
9. customThe crude product is chromatographed
10. washeluting with 0-40% EtOAc in heptane (300 mL each 10%)