1,8-Diazabicyclo(5.4.0)undec-7-ene → (+/-)-4-(4-Fluorophenyl)-5-(pyridin-4-yl)-1-(1,2,3,5,6,7,8,8a-octahydroindolizin-7-yl)imidazole

HRID 9874Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 9874
C1(C)C=CC(S([CH:10]([N+:18]#[C-:19])[C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)(=O)=O)=CC=1.[N:21]1[CH:26]=[CH:25][C:24]([CH:27]=[N:28][CH:29]2[CH2:37][CH:36]3[N:32]([CH2:33][CH2:34][CH2:35]3)[CH2:31][CH2:30]2)=[CH:23][CH:22]=1.C1CCN2C(=NCCC2)CC1>ClCCl>[F:17][C:14]1[CH:13]=[CH:12][C:11]([C:10]2[N:18]=[CH:19][N:28]([CH:29]3[CH2:37][CH:36]4[N:32]([CH2:33][CH2:34][CH2:35]4)[CH2:31][CH2:30]3)[C:27]=2[C:24]2[CH:23]=[CH:22][N:21]=[CH:26][CH:25]=2)=[CH:16][CH:15]=1

Komponenten

5

Edukt 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 10827289a-Tosyl-(4-fluorobenzyl) isocyanideHCID 21988493(+/-)-7-(4-Pyridylmethyleneamino)-1,2,3,5,6,7,8,8a-octahydroindolizine

Produkt 1

HCID 10133267(+/-)-4-(4-Fluorophenyl)-5-(pyridin-4-yl)-1-(1,2,3,5,6,7,8,8a-octahydroindolizin-7-yl)imidazoleAusbeute 14,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

α-(p-Toluenesulfonyl)-4-fluorobenzylisocyanide (10.1 g, 34.9 mmol) and (±)-7-(4-pyridylmethyleneamino)-1,2,3,5,6,7,8,8a-octahydroindolizine (8.0 g (34.9 mmol), prepared as described in 2)) were dissolved in dichloromethane (150 ml). To the solution was added 1,8-diazabicyclo[5.4.0]-7-undecene (5.22 ml, 34.9 mmol), and the resulting mixture was stirred at room temperature for 2 hours. At the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure. To the residue was added a saturated aqueous solution of sodium hydrogencarbonate and this was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate and the solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography through silica gel (eluent, ethyl acetate:methanol:isopropylamine=20:1:1), to give the title compound (1.87 g) as a pale yellow powder (yield 14%).

Aufarbeitung

  1. concentrationAt the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure
  2. additionTo the residue was added a saturated aqueous solution of sodium hydrogencarbonate
  3. extractionthis was extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was removed by distillation under reduced pressure
  7. customThe residue was purified by column chromatography through silica gel (eluent, ethyl acetate:methanol:isopropylamine=20:1:1)

Quellen und Nachweise

ORD-Eintrag
ord-8666654f56c240ce8062fe43832322e8
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091352B2

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