反应详情

1-(4-Hydroxy-4-[1-triisopropylsilyl-1H-indol-5-yl]-piperidin-1-yl)ethanone (3.11 g, 7.4 mmol) in dichloromethane (100 ml) was treated with pyridinium p-toluenesulfonate (3.8 g, 15.1 mmol) and stirred for 72 hours. The solution was poured into water and extracted with dichloromethane (100 ml). The extractions were dried (MgSO4), concentrated and the crude product purified by flash chromatography using ethyl acetate as eluant, to give 1-(4-[1-triisopropylsilyl-1H-indol-5-yl]-1,2,3,6-tetrahydropyridin-1-yl)-ethanone (1.95 g, 66%) as a white solid; δH (CDCl3) 0.80 (18H, d, J 8.5 Hz, 6×CH3), 1.30 (3H, m, 3×CH), 1.75 (3H, d, J 6.7 Hz, COCH3), 2.30 (2H, m, tetrahydropyridinyl H), 3.25 (1H, t, J 5.6 Hz, tetrahydropyridinyl H), 3.40 (1H, t, J 5.6 Hz, tetrahydropyridinyl H), 3.75 (1H, m, tetrahydropyridyl H), 3.85 (1H, m, tetrahydropyridyl H), 5.60 (1H, m, CH=CR), 6.20 (1H, d, J 2.2 Hz, ArH), 6.80 (2H, m, ArH), 7.00 (1H, d, J 7.3 Hz, ArH), and 7.20 (1H, m, ArH).

1. extractionextracted with dichloromethane (100 ml)
2. extractionThe extractions
3. dry with materialwere dried (MgSO4)
4. concentrationconcentrated
5. customthe crude product purified by flash chromatography