phenyl N-benzyloxycarbamate → 1-(N-benzyloxycarbamoyl)-3-(3,5-di-tert-butyl-4-hydroxybenzylidene)pyrrolidin-2-one

HRID 1109292Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1109292
[C:1]([C:5]1[CH:6]=[C:7]([CH:15]=[C:16]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:17]=1[OH:18])[CH:8]=[C:9]1[CH2:13][CH2:12][NH:11][C:10]1=[O:14])([CH3:4])([CH3:3])[CH3:2].[CH2:23]([O:30][NH:31][C:32](=O)[O:33]C1C=CC=CC=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>N1C=CC=CC=1>[CH2:23]([O:30][NH:31][C:32]([N:11]1[CH2:12][CH2:13][C:9](=[CH:8][C:7]2[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:17]([OH:18])=[C:16]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:15]=2)[C:10]1=[O:14])=[O:33])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Komponenten

4

Edukt 2

HCID 11644415phenyl N-benzyloxycarbamateHCID 538962973-(3,5-Di-tert-butyl-4-hydroxybenzylidene)-2-pyrrolidone

Produkt 1

HCID 538058911-(N-benzyloxycarbamoyl)-3-(3,5-di-tert-butyl-4-hydroxybenzylidene)pyrrolidin-2-oneAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

3-(3,5-Di-tert-butyl-4-hydroxybenzylidene)pyrrolidin-2-one (600 mg, 2 mmole) and phenyl N-benzyloxycarbamate (490 mg, 2.01 mmole) were dissolved into 8 ml of pyridine and the solution was heated under reflux for 12 hours. The reaction mixture was evaporated and the obtained residue was dissolved into ethyl acetate, which was washed with an aqueous solution of 0.1N hydrochloric acid, water, and saturated brine, dried over magnesium sulfate, and evaporated. The obtained residue was separated by using silica gel chromatography (toluene:ethyl acetate=10:1) and recrystallized from dichloromethane/n-hexane, whereby 550 mg of the objective compound (Ia-10) was obtained in 61% yield.

Aufarbeitung

  1. temperaturethe solution was heated
  2. temperatureunder reflux for 12 hours
  3. customThe reaction mixture was evaporated
  4. dissolutionthe obtained residue was dissolved into ethyl acetate, which
  5. washwas washed with an aqueous solution of 0.1N hydrochloric acid, water, and saturated brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. customThe obtained residue was separated
  9. customrecrystallized from dichloromethane/n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-e0e1b7afab6d407aab8c805ffb493e9d
Quelldatensatz
uspto-grants-1994_06
Patentnummer
US05319100

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