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Ethyl 4-(1-benzyloxycarbonyl-4-piperidyl)-2-chlorobutyrate → 4-Piperidinebutanoic acid, ethyl ester

HRID 980606
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 980606
C(OC([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][CH:19](Cl)[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:13][CH2:12]1)=O)C1C=CC=CC=1>C(O)C.[C].[Pd]>[NH:11]1[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:13][CH2:12]1
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Komponenten

4

Edukt 1

HCID 20143712Ethyl 4-(1-benzyloxycarbonyl-4-piperidyl)-2-chlorobutyrate

Produkt 1

HCID 106318484-Piperidinebutanoic acid, ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418390HCID 178418390, VerbindungKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

In 20 ml of ethanol is dissolved 10.5 g of ethyl 4-(1-benzyloxycarbonyl -4-piperidyl)-2-chlorobutyrate, and a catalytic reduction reaction is carried out at ordinary temperature and at atmosphereic pressure using 5 g of 10% palladium-carbon (50% in water ) as a catalyst. After absorption of hydrogen stops, the catalyst is removed by filtration, and the filtrate is concentrated under reduced pressure to give ethyl 4-(4-piperidyl)butyrate. This product is dissolved in a mixture of 200 ml of ethyl acetate and 100 ml of water, 6 g of sodium hydrogencarbonate is added to the solution, followed by stirring at room temperature. Benzyloxycarbonyl chloride (6 ml) is added dropwise to the mixture, and after the addition is completed, the mixture is stirred at room temperature for 1.5 hours. The ethyl acetate layer is separated, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue is purified by silica-gel column chromatography (hexane:ethyl acetate=3:1) to give 5.3 g of ethyl 4-(1-benzyloxycarbonyl-4 -piperidyl)butyrate as a colorless oily material.

Aufarbeitung

  1. customa catalytic reduction reaction
  2. customAfter absorption of hydrogen
  3. customthe catalyst is removed by filtration
  4. concentrationthe filtrate is concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-3fac9d0963854b0ebeb453380866eee2
Quelldatensatz
uspto-grants-1987_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04638000

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