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1-[(2-Methoxy-3-pyridinyl)methyl]-4-piperidinecarboxaldehyde → 1-[(2-Methoxy-3-pyridinyl)methyl]-4-[(E)-2-[2-(cyclopentyloxy)phenyl]-1-ethenyl]piperidine

HRID 1837765
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1837765
[CH:1]1([O:6][C:7]2[CH:21]=[CH:20][CH:19]=[CH:18][C:8]=2[CH2:9]P(=O)(OCC)OCC)[CH2:5][CH2:4][CH2:3][CH2:2]1.CC(C)([O-])C.[K+].[CH3:28][O:29][C:30]1[C:35]([CH2:36][N:37]2[CH2:42][CH2:41][CH:40]([CH:43]=O)[CH2:39][CH2:38]2)=[CH:34][CH:33]=[CH:32][N:31]=1>O1CCCC1>[CH3:28][O:29][C:30]1[C:35]([CH2:36][N:37]2[CH2:42][CH2:41][CH:40](/[CH:43]=[CH:9]/[C:8]3[CH:18]=[CH:19][CH:20]=[CH:21][C:7]=3[O:6][CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)[CH2:39][CH2:38]2)=[CH:34][CH:33]=[CH:32][N:31]=1
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Komponenten

5

Edukt 3

HCID 226784071-[(2-Methoxy-3-pyridinyl)methyl]-4-piperidinecarboxaldehydeHCID 22678615Diethyl 2-(cyclopentyloxy)benzylphosphonateHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 226784561-[(2-Methoxy-3-pyridinyl)methyl]-4-[(E)-2-[2-(cyclopentyloxy)phenyl]-1-ethenyl]piperidineAusbeute 56,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel
2×

Versuchsvorschrift

786 mg of diethyl 2-(cyclopentyloxy)benzylphosphonate was dissolved in 10 ml of tetrahydrofuran. To the mixture was added 281 mg of potassium tert-butoxide, followed by stirring for 15 minutes under ice-cooling. A solution of 500 mg of 1-[(2-methoxy-3-pyridinyl)methyl]-4-piperidinecarboxaldehyde dissolved in 3 ml of tetrahydrofuran was added dropwise thereinto, followed by stirring at room temperature for 2 hours. Ice water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated, and the resulting crude product was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1), to give 473 mg of the title compound as a pale yellow oil.

Aufarbeitung

  1. temperaturecooling
  2. additionwas added dropwise
  3. stirringby stirring at room temperature for 2 hours
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated
  8. customthe resulting crude product was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1)

Quellen und Nachweise

ORD-Eintrag
ord-c884a983e8b3446dbabd9639c5307e8f
Quelldatensatz
uspto-grants-2004_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06784192B2

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