Benzyl chloroformate → 4-Oxo-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid benzyl ester

HRID 1934484Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1934484
[CH2:1]([O:8][C:9](Cl)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N:19]1[CH2:26][CH:25]2[CH:21]([CH2:22][CH2:23][C:24]2=[O:27])[CH2:20]1)C1C=CC=CC=1>ClCCl>[CH2:1]([O:8][C:9]([N:19]1[CH2:26][CH:25]2[CH:21]([CH2:22][CH2:23][C:24]2=[O:27])[CH2:20]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 10387Benzyl chloroformate2×HCID 134637692-Benzylhexahydrocyclopenta[c]pyrrol-4(1H)-one

Produkt 1

HCID 185091484-Oxo-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid benzyl esterAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Benzyloxycarbonyl chloride (5.14 ml, 36.0 mmol) was added dropwise to a solution of 7-benzyl-2-oxo-7-azabicyclo[3.3.0]octane (5.20 g, 24.2 mmol) in dichloromethane (50 ml) under cooling with ice, followed by stirring at room temperature for 24 hours. The mixture was again cooled with ice, and benzyloxycarbonyl chloride (5.14 ml, 36.0 mmol) was added thereto dropwise. After removing the solvent by evaporation, the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1) to give 4.52 g (17.4 mmol, 72%) of the title compound as a colorless oily substance.

Aufarbeitung

  1. temperatureunder cooling with ice
  2. additionwas added
  3. customAfter removing the solvent
  4. customby evaporation
  5. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1)

Quellen und Nachweise

ORD-Eintrag
ord-3998ef7cc5b24d0fb3483f812291470c
Quelldatensatz
uspto-grants-2002_05
Patentnummer
US06384050B1

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