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

4-Methylbenzenethiol → (+/-)-1-(t-Butoxycarbonyl)-2-[4-(p-toluenesulfonyl)-2-oxobutyl]pyrrolidine

HRID 9886
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 9886
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[CH2:13][C:14](=[O:17])[CH:15]=[CH2:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].CC1C=CC(S)=CC=1.Cl[C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([C:33](OO)=O)[CH:28]=1.[S:37]([O-])([O-:40])(=[O:39])=S.[Na+].[Na+].C(=O)([O-])O.[Na+]>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[CH2:13][C:14](=[O:17])[CH2:15][CH2:16][S:37]([C:32]1[CH:31]=[CH:30][C:29]([CH3:33])=[CH:28][CH:27]=1)(=[O:40])=[O:39])=[O:7])([CH3:4])([CH3:3])[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 78114-MethylbenzenethiolHCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 21988503Tert-butyl 2-(2-oxobut-3-EN-1-YL)pyrrolidine-1-carboxylate

Produkt 1

HCID 21988484
(+/-)-1-(t-Butoxycarbonyl)-2-[4-(p-toluenesulfonyl)-2-oxobutyl]pyrrolidine
Ausbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

(±)-1-(t-Butoxycarbonyl)-2-(2-oxo-3-butenyl)pyrrolidine (206 mg (10.86 mmol), prepared as described in Reference example 1–2)) was dissolved in tetrahydrofuran (2 ml). To the solution was added 4-methylthiophenol (107 mg, 0.86 mmol), and the resulting mixture was stirred at room temperature for 2 hours. At the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure, and the resulting residue was dissolved in dichloromethane (2 ml). To the resulting mixture was added 70 wt % m-chloroperbenzoic acid (468 mg, 1.894 mmol) by portions under ice cooling, and the resulting mixture was stirred at room temperature for 2 hours. To the mixture were added an aqueous solution of 10% sodium thiosulfate and a saturated aqueous solution of sodium hydrogencarbonate in that order, and the resulting mixture was stirred and extracted with dichloromethane. The organic layer was washed with water, dried over anhydrous magnesium sulfate and the solvent was removed by distillation under reduced pressure, to give the title compound (322 mg) as a colorless oil (yield 94%).

Aufarbeitung

  1. concentrationAt the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure
  2. dissolutionthe resulting residue was dissolved in dichloromethane (2 ml)
  3. stirringthe resulting mixture was stirred at room temperature for 2 hours
  4. extractionextracted with dichloromethane
  5. washThe organic layer was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was removed by distillation under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-82f6431d8ef44e6fb7bc43c55597e2a3
Quelldatensatz
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07091352B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion