반응 #1911020

반응 방정식

sodium bicarbonate

methyl-4-methylbenzenesulfonate

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

dimethylformamide tetrahydrofuran

→

title compound

3-[1-(8-Methoxy-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl)-1,2,3,6-tetrahydro-pyridin-4-yl]-1H-indole

반응 조건

후처리

1. 1
   workup.ADDITIONadded
2. 2
   온도The reaction mixture was refluxed under nitrogen for 18 hours
3. 3
   온도cooled
4. 4
   농축concentrated in vacuum
5. 5
   기타The residue was partitioned between 400 mL each of water and ethyl acetate
6. 6
   기타The layers were separated
7. 7
   세척The organic phase was washed with water and saturated aqueous sodium chloride solution
8. 8
   건조dried over anhydrous potassium carbonate
9. 9
   기타evaporated to a foam (1.0 g)
10. 10
    기타Trituration with ether yielded a solid which
11. 11
    기타was recrystallized

실험 절차

(2R)-8-Methoxy-2,3-dihydro-benzo[1,4]dioxin-2-yl]methyl-4-methylbenzenesulfonate (1.1 g, 3.1 mmole) was dissolved in a mixture of dimethylformamide/tetrahydrofuran (1:1 v/v, 50 mL) and 3-(1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole (0.60 g 1.6 mmole) added, followed by sodium bicarbonate (1.0 g). The reaction mixture was refluxed under nitrogen for 18 hours, then cooled and concentrated in vacuum. The residue was partitioned between 400 mL each of water and ethyl acetate. The layers were separated. The organic phase was washed with water and saturated aqueous sodium chloride solution, dried over anhydrous potassium carbonate and evaporated to a foam (1.0 g). Trituration with ether yielded a solid which was recrystallized from boiling chloroform/methanol (1:1 v/v) to give 0.40 g (40%) of the (S)-enantiomer of the title compound as an off-white solid one-quarter hydrate, m.p. 203–205° C.

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