StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

1,4-Dibromo-2-butanol → (4aRS,5SR,8aRS)-1-benzyl-5-(3-hydroxypyrrolidin-1-yl)perhydroquinoxaline-2,3-dione

HRID 1876803
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1876803
[NH2:1][CH:2]1[CH2:11][CH2:10][CH2:9][CH:8]2[CH:3]1[NH:4][C:5](=[O:20])[C:6](=[O:19])[N:7]2[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])(O)=O.[Na+].Br[CH2:27][CH:28]([OH:32])[CH2:29][CH2:30]Br>C(#N)C>[CH2:12]([N:7]1[CH:8]2[CH:3]([CH:2]([N:1]3[CH2:30][CH2:29][CH:28]([OH:32])[CH2:27]3)[CH2:11][CH2:10][CH2:9]2)[NH:4][C:5](=[O:20])[C:6]1=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 295701,4-Dibromo-2-butanolHCID 516892Sodium BicarbonateHCID 68777664(4aRS,5SR,8aRS)-5-amino-1-benzylperhydroquinoxaline-2,3-dione

Produkt 1

HCID 68778432(4aRS,5SR,8aRS)-1-benzyl-5-(3-hydroxypyrrolidin-1-yl)perhydroquinoxaline-2,3-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

(4aRS,5SR,8aRS)-5-Amino-1-benzylperhydroquinoxaline-2,3-dione (144 mg, 0.53 mmol) was dissolved in acetonitrile (16 ml), and NaHCO3 (300 mg, 3.57 mmol) and racemic 1,4-dibromobutan-2-ol (purity 85%, 1.15 g, 4.20 mmol, 0.57 ml) were added. After 24 hours, NaHCO3 was separated off and the mixture was evaporated in vacuo. The solid was taken up in CH2Cl2 and the mixture was extracted by shaking three times with HCl (1 N). The aqueous phase was then brought to pH 8 with NaOH (2 N) and extracted by shaking three times with CH2Cl2. The organic phases were dried over Na2SO4 and evaporated in vacuo. The crude product was purified by flash chromatography over silica gel 60 (40-63 μm, (Merck) Ø 2 cm, acetone/MeOH/Et2NH 9.5:0.5:0.1, l=17 cm, V=5 ml). A pale yellow solid was isolated.

Aufarbeitung

  1. customNaHCO3 was separated off
  2. customthe mixture was evaporated in vacuo
  3. extractionthe mixture was extracted
  4. extractionextracted
  5. stirringby shaking three times with CH2Cl2
  6. dry with materialThe organic phases were dried over Na2SO4
  7. customevaporated in vacuo
  8. customThe crude product was purified by flash chromatography over silica gel 60 (40-63 μm, (Merck) Ø 2 cm, acetone/MeOH/Et2NH 9.5:0.5:0.1, l=17 cm, V=5 ml)
  9. customA pale yellow solid was isolated

Quellen und Nachweise

ORD-Eintrag
ord-7d8d99e8c42741f1b0735069a8d4fb7c
Quelldatensatz
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08309725B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion