Toluene → Agn-PC-00bqth

HRID 566373Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 566373
C1(C)C=CC=CC=1.[C:8]1([CH:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:17][CH2:16][N:15]2[C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[N:29]12CC[CH:32]([CH2:33][CH2:34]1)[CH:31](O)[CH2:30]2.[H-].[Na+]>[Cl-].[Na+].O>[C:8]1([CH:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:17][CH2:16][N:15]2[C:24]([O:26][CH:27]2[CH:32]3[CH2:33][CH2:34][N:29]([CH2:30][CH2:31]3)[CH2:28]2)=[O:25])[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Komponenten

6

Edukt 4

HCID 1140TolueneHCID 15381(+-)-3-QuinuclidinolHCID 24758Sodium hydrideHCID 10423841Ethyl 1-phenyl-3,4-dihydro-1H-isoquinoline-2-carboxylate

Produkt 1

HCID 9885319Agn-PC-00bqthAusbeute 12,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

To a 30 ml toluene solution containing 0.70 g of ethyl 1-phenyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylate and 0.41 g of 3-quinuclidinol, 0.03 g of sodium hydride (60%) was added. The resulting mixture was stirred at 140° C. for 2 days while removing the ethanol formed. The reaction mixture was cooled to room temperature, brine was added, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform:methanol=10:1→chloroform:methanol:28% aqueous ammonia=10:1:0.1), thereby 0.11 g of 3-quinuclidinyl 1-phenyl-1,2,3,4-tetrahydro-2-isoquinolinecarboxylate was obtained as yellow oil. The resulting oil was dissolved in 10 ml of ethanol, followed by the addition of 27 mg of oxalic acid. Then, the solvent was removed under reduced pressure. The resulting solid was recrystallized from isopropanol and isopropyl ether, thereby 0.08 g of 3-quinuclidinyl 1-phenyl-1,2,3,4-tetrahydro-2-isoquinolinecarboxylate monooxalate was obtained as colorless crystals.

Aufarbeitung

  1. additionwas added
  2. customwhile removing the ethanol
  3. customformed
  4. temperatureThe reaction mixture was cooled to room temperature
  5. extractionthe mixture was extracted with ethyl acetate
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. customthe solvent was removed under reduced pressure
  8. customThe resulting residue was purified by silica gel column chromatography (chloroform:methanol=10:1→chloroform:methanol:28% aqueous ammonia=10:1:0.1)

Quellen und Nachweise

ORD-Eintrag
ord-33004775a7bd49f1a7ab256e3a35bf75
Quelldatensatz
uspto-grants-2001_01
Patentnummer
US06174896B1

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