반응 #1911024

반응 방정식

sodium bicarbonate

[(2R)-7-Methoxy-2,3-dihydro-benzo[1,4]dioxin-2-yl]methyl 4-methylbenzenesulfonate

3-(1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole

→

title compound

3-(1-{[7-Methoxy-2,3-dihydro-1,4-benzodioxin-2-yl]methyl}-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole

용매

dimethylformamide tetrahydrofuran

반응 조건

후처리

1. 1
   workup.ADDITIONadded
2. 2
   온도the mixture was refluxed under nitrogen for 18 hours
3. 3
   기타The solvent was removed under vacuum
4. 4
   기타the residue partitioned between 400 mL each of methylene chloride and water
5. 5
   기타The layers were separated
6. 6
   세척the organic phase was washed with water and saturated sodium chloride solution
7. 7
   건조dried over potassium carbonate
8. 8
   여과filtered
9. 9
   기타The filtrate was evaporated to a foam (1.6 g)

실험 절차

[(2R)-7-Methoxy-2,3-dihydro-benzo[1,4]dioxin-2-yl]methyl 4-methylbenzenesulfonate (1.5 g, 4.3 mmole) was dissolved in a mixture of dimethylformamide/tetrahydrofuran (1:1 v/v, 30 mL) and 3-(1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole (0.80 g, 4.0 mmole) added, followed by sodium bicarbonate (1.0 g), and the mixture was refluxed under nitrogen for 18 hours. The solvent was removed under vacuum and the residue partitioned between 400 mL each of methylene chloride and water. The layers were separated and the organic phase was washed with water and saturated sodium chloride solution, dried over potassium carbonate and filtered. The filtrate was evaporated to a foam (1.6 g). Chromatography on silica gel using 4% methanol in chloroform as eluant gave 0.20 g of the (S)-enantiomer of the title compound as a yellow solid, m.p. 166–168° C.

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