反应详情

A mixture of tryptamine hydrochloride (1.96 g, 10 mmol), ethyl 3-bromopyruvate (1.67 mL, 1.2 equiv) and decolorizing charcoal (0.5 g) in absolute ethanol was heated to reflux under nitrogen overnight. TEA was added and the reaction mixture was heated to reflux for another 7.5 hours. After cooling, charcoal was removed by filtration and washed with ethanol. The filtrate was concentrated under vacuum and diluted with water (20 mL). It was then extracted by EtOAc (3×30 mL) and the combined organic layers were washed with brine and dried over MgSO4. Evaporation of solvent and recrystallization from DCM-Hexane gave the title compound (1.17 g). 1H-NMR (CDCl3): δ 10.49 (1 H, br s), 7.79 (1H, d), 7.43 (1H, d), 7.43 (1H, d), 7.06 (2H, m), 5.27 (1H, br s), 4.29 (2H, q) 3.58 (2H, m), 3.17 (2H, m), 1.36 (3H, t); MS (ES): 257 (MH+).

1. temperaturewas heated
2. temperatureto reflux under nitrogen overnight
3. additionTEA was added
4. temperaturethe reaction mixture was heated
5. temperatureto reflux for another 7.5 hours
6. temperatureAfter cooling
7. customcharcoal was removed by filtration
8. washwashed with ethanol
9. concentrationThe filtrate was concentrated under vacuum
10. additiondiluted with water (20 mL)
11. extractionIt was then extracted by EtOAc (3×30 mL)
12. washthe combined organic layers were washed with brine
13. dry with materialdried over MgSO4
14. customEvaporation of solvent and recrystallization from DCM-Hexane