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Acetic Acid → Tert-butyl 1-benzyl-8-ethylamino-1,2,3,4-tetrahydro-2-oxoquinolin-3-ylcarbamate

HRID 2070127
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2070127
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:9](=[O:19])[CH:8]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:7]2.[CH:28](=O)[CH3:29].C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[CH2:12]([N:10]1[C:11]2[C:6](=[CH:5][CH:4]=[CH:3][C:2]=2[NH:1][CH2:28][CH3:29])[CH2:7][CH:8]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:24])([CH3:26])[CH3:25])[C:9]1=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 177AcetaldehydeHCID 5003444Sodium cyanoborohydrideHCID 59620406Tert-butyl 8-amino-1-benzyl-1,2,3,4-tetrahydro-2-oxoquinolin-3-ylcarbamate

Produkt 1

HCID 59620343Tert-butyl 1-benzyl-8-ethylamino-1,2,3,4-tetrahydro-2-oxoquinolin-3-ylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887
Methanol
Lösungsmittel

Versuchsvorschrift

tert-Butyl 8-amino-1-benzyl-1,2,3,4-tetrahydro-2-oxoquinolin-3-ylcarbamate (1.0 g) was dissolved in methanol (10 mL), and acetaldehyde (599 mg), acetic acid (10 mg), and sodium cyanoborohydride (171 mg) were sequentially added to the solution under cooling on ice. The mixture was stirred at room temperature for 30 minutes, and the reaction mixture was concentrated under reduced pressure. The thus-recovered residue was dissolved in ethyl acetate, and the solution was sequentially washed with water, saturated aqueous sodium bicarbonate solution, and saturated aqueous sodium chloride solution. The organic layer was dried over sodium sulfate, and solvent was evaporated under reduced pressure. The recovered residue was purified through silica gel column chromatography (ethyl acetate: n-hexane=1:3), whereby the title compound (600 mg) was yielded.

Aufarbeitung

  1. temperatureunder cooling on ice
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. dissolutionThe thus-recovered residue was dissolved in ethyl acetate
  4. washthe solution was sequentially washed with water, saturated aqueous sodium bicarbonate solution, and saturated aqueous sodium chloride solution
  5. dry with materialThe organic layer was dried over sodium sulfate, and solvent
  6. customwas evaporated under reduced pressure
  7. customThe recovered residue was purified through silica gel column chromatography (ethyl acetate: n-hexane=1:3), whereby the title compound (600 mg)
  8. customwas yielded

Quellen und Nachweise

ORD-Eintrag
ord-6fccba938ebf4986a6f22190b5251d71
Quelldatensatz
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08299255B2

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