반응 #77531

반응 방정식

(2R)-2,3,8,9-tetrahydrofuro[3,2-f][1,4]benzodioxin-2-ylmethyl 4-methylbenzenesulfonate

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

ethyl acetate

→

title compound

3-{1-[2,3,8,9-Tetrahydrofuro[3,2-f][1,4]benzodioxin-2-ylmethyl]-1,2,3,6-tetrahydro-4-pyridinyl}-1H-indole

용매

DMSO

반응 조건

후처리

1. 1
   세척the solution was washed with 250 mL portions of saturated aqueous sodium bicarbonate, water and saturated brine
2. 2
   건조dried over sodium sulfate
3. 3
   여과filtered
4. 4
   농축concentrated in vacuum
5. 5
   기타chromatographed on silica gel with 2% methanol in chloroform

실험 절차

A solution of 0.65 g (1.8 mmole) of (2R)-2,3,8,9-tetrahydrofuro[3,2-f][1,4]benzodioxin-2-ylmethyl 4-methylbenzenesulfonate and 1.0 g (5.0 mmole) of 3-(1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole in 10 mL of DMSO was heated under nitrogen at 80° C. for 4 hours. After the reaction had cooled to room temperature, 400 mL of ethyl acetate was added and the solution was washed with 250 mL portions of saturated aqueous sodium bicarbonate, water and saturated brine, dried over sodium sulfate, filtered and concentrated in vacuum. The residue was column chromatographed on silica gel with 2% methanol in chloroform to give 0.32 g of the (S)-enantiomer of the title compound as a gold solid, m.p. 207-209° C.

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