反応 #77531

反応方程式

(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

溶媒

DMSO

反応条件

後処理

1. 1
   洗浄the solution was washed with 250 mL portions of saturated aqueous sodium bicarbonate, water and saturated brine
2. 2
   乾燥dried over sodium sulfate
3. 3
   ろ過filtered
4. 4
   濃縮concentrated in vacuum
5. 5
   その他chromatographed on silica gel with 2% methanol in chloroform

実験手順

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.

出典