(2-Methylsulfonylbenzyl)triphenylphosphonium chloride → 1-[(2-Methoxy-3-pyridyl)methyl]-4-[2-(methylsulfonyl)phenethyl]piperidine

HRID 1837724Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1837724
[CH3:1][O:2][C:3]1[C:8]([CH2:9][N:10]2[CH2:15][CH2:14][CH:13]([CH:16]=O)[CH2:12][CH2:11]2)=[CH:7][CH:6]=[CH:5][N:4]=1.[Cl-].[CH3:19][S:20]([C:23]1[CH:48]=[CH:47][CH:46]=[CH:45][C:24]=1[CH2:25][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)(=[O:22])=[O:21].CC(C)([O-])C.[K+].[H][H]>CN(C)C=O.C(O)C.[C].[Pd].O>[CH3:1][O:2][C:3]1[C:8]([CH2:9][N:10]2[CH2:15][CH2:14][CH:13]([CH2:16][CH2:25][C:24]3[CH:45]=[CH:46][CH:47]=[CH:48][C:23]=3[S:20]([CH3:19])(=[O:22])=[O:21])[CH2:12][CH2:11]2)=[CH:7][CH:6]=[CH:5][N:4]=1

Komponenten

9

Edukt 4

HCID 22678327(2-Methylsulfonylbenzyl)triphenylphosphonium chlorideHCID 226784071-[(2-Methoxy-3-pyridinyl)methyl]-4-piperidinecarboxaldehydeHCID 23665647Potassium tert-butoxideHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 226785581-[(2-Methoxy-3-pyridyl)methyl]-4-[2-(methylsulfonyl)phenethyl]piperidineAusbeute 62,6 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418390HCID 178418390, VerbindungKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

3.90 g of 1-[(2-methoxy-3-pyridyl)methyl]-4-piperidinecarboxaldehyde, 8.92 g of (2-methylsulfonylbenzyl)triphenylphosphonium chloride and 1.96 g of potassium tert-butoxide were suspended in 80 ml of N,N-dimethylformamide, and the mixture was stirred for 3 hours at room temperature. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated, and the crude product was purified by NH form silica gel column chromatography (ethyl acetate:hexane=1:4). The resulting product and 440 mg of 10% palladium-carbon powder (water-containing product) were suspended in 80 ml of ethanol. After replacing the atmosphere of a container with hydrogen, the mixture was stirred at room temperature under normal pressure for 30 minutes. The reaction solution was filtered, and the filtrate was evaporated, to give 4.05 g of the title compound as a colorless oil.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe crude product was purified by NH
  6. customform silica gel column chromatography (ethyl acetate:hexane=1:4)
  7. stirringthe mixture was stirred at room temperature under normal pressure for 30 minutes
  8. filtrationThe reaction solution was filtered
  9. customthe filtrate was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-b6b2fdde38bf49c48b78d8644be4ed69
Quelldatensatz
uspto-grants-2004_08
Patentnummer
US06784192B2

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