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

Sodium hydride → Tert-butyl 4-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-3-oxopiperazine-1-carboxylate

HRID 2105882
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2105882
[H-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][NH:13][C:12](=[O:16])[CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].Br[CH2:18][CH2:19][O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22]>CN(C)C=O>[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][N:13]([CH2:18][CH2:19][O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])[C:12](=[O:16])[CH2:11]1)=[O:9])([CH3:6])([CH3:4])[CH3:5]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 3157178Tert-butyl 3-oxopiperazine-1-carboxylateHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilane

Produkt 1

HCID 68638537Tert-butyl 4-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-3-oxopiperazine-1-carboxylateAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Sodium hydride (0.35 g, 8.6 mmol, 60% in mineral oil) was added to a solution of 4-tert-butyloxycarbonyl-piperazin-2-one (0.86 g, 4.3 mmol) in dimethylformamide (20.0 mL) at 0° C. The reaction was stirred at 0° C. for 0.5 h. To this mixture was added 2-bromoethoxy-tert-butyldimethylsilane (2.3 mL, 10.8 mmol) and the reaction was stirred for 2 h at room temperature. The reaction mixture was quenched with a dilute aqueous solution of sodium bicarbonate and extracted with methylene chloride. The organic extracts were washed with brine and dried over anhydrous sodium sulfate. Purification of the crude residue by flash column chromatography (silica gel, eluting with 20% ethyl acetate in hexanes) gave 4-tert-butyloxycarbonyl-1-[2-(tert-butyldimethylsilyloxy)ethyl]-piperazin-2-one (1.17 g, 76%).

Aufarbeitung

  1. stirringthe reaction was stirred for 2 h at room temperature
  2. customThe reaction mixture was quenched with a dilute aqueous solution of sodium bicarbonate
  3. extractionextracted with methylene chloride
  4. washThe organic extracts were washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customPurification of the crude residue
  7. washby flash column chromatography (silica gel, eluting with 20% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-a09c86b8619a4693b223ead4edce6b44
Quelldatensatz
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07579368B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion