反应详情

To a cold solution of methyl indole-5-carboxylate (2 g, 11.4 mmol) in glacial acetic acid at 0° C. (15 ml) sodium cyanoborohydride (1.075 g, 17.1 mmol) was slowly added. The mixture was allowed to warm-up and stirred at room temperature for one more hour, cooled again to 0° C. and quenched with H2O. The pH of the resultant solution was adjusted to the value of 12 by adding aqueous NaOH, extracted with DCM, washed with brine and dried over MgSO4. The dried extract was concentrated in vacuum and purified by flash chromatography (eluent 30% EtOAc in hexane) to give the title compound 20 (1.62 g, 80%) as a beige solid. 1H-NMR (DMSO) δ: 2.94 (t, J=8.6 Hz, 2H); 3.51 (dt, J=1.2, 8.6 Hz, 2H); 3.71 (s, 3H); 6.42 (d, J=8.0 Hz, 2H); 7.54 (m, 2H).

1. temperatureto warm-up
2. temperaturecooled again to 0° C.
3. customquenched with H2O
4. additionby adding aqueous NaOH
5. extractionextracted with DCM
6. washwashed with brine
7. dry with materialdried over MgSO4
8. extractionThe dried extract
9. concentrationwas concentrated in vacuum
10. custompurified by flash chromatography (eluent 30% EtOAc in hexane)