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

HRID 49253Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 49253
CC1C=CC(S(O[CH2:12][C@H:13]2[CH2:18][O:17][C:16]3[CH:19]=[CH:20][C:21]4[O:25][CH2:24][CH2:23][C:22]=4[C:15]=3[O:14]2)(=O)=O)=CC=1.[NH:26]1[CH2:31][CH:30]=[C:29]([C:32]2[C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[NH:34][CH:33]=2)[CH2:28][CH2:27]1.C(OCC)(=O)C>CS(C)=O>[O:14]1[C:15]2[C:22]3[CH2:23][CH2:24][O:25][C:21]=3[CH:20]=[CH:19][C:16]=2[O:17][CH2:18][CH:13]1[CH2:12][N:26]1[CH2:27][CH:28]=[C:29]([C:32]2[C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[NH:34][CH:33]=2)[CH2:30][CH2:31]1

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 27610233-(1,2,3,6-Tetrahydropyridin-4-yl)-1H-indoleHCID 86586535(2R)-2,3,8,9-tetrahydrofuro[3,2-f][1,4]benzodioxin-2-ylmethyl 4-methylbenzenesulfonate

Produkt 1

HCID 101783553-{1-[2,3,8,9-Tetrahydrofuro[3,2-f][1,4]benzodioxin-2-ylmethyl]-1,2,3,6-tetrahydro-4-pyridinyl}-1H-indole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. washthe solution was washed with 250 mL portions of saturated aqueous sodium bicarbonate, water and saturated brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuum
  5. customchromatographed on silica gel with 2% methanol in chloroform

Quellen und Nachweise

ORD-Eintrag
ord-db03a09d6d574ea78f2d4bc4285fbade
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06706736B2

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