Dimethylformamide → 1-Tert-butyl 3-ethyl 3-benzyl-4-oxopiperidine-1,3-dicarboxylate

HRID 1279252Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1279252
[CH2:1]([O:3][C:4]([CH:6]1[C:11](=[O:12])[CH2:10][CH2:9][N:8]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:7]1)=[O:5])[CH3:2].CN(C=O)C.[CH2:25](Br)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>>[CH2:1]([O:3][C:4]([C:6]1([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:11](=[O:12])[CH2:10][CH2:9][N:8]([C:13]([O:15][C:16]([CH3:18])([CH3:17])[CH3:19])=[O:14])[CH2:7]1)=[O:5])[CH3:2]

Komponenten

4

Edukt 3

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 64208761-(1,1-Dimethylethyl) 3-ethyl 4-oxo-1,3-piperidinedicarboxylate

Produkt 1

HCID 541303761-Tert-butyl 3-ethyl 3-benzyl-4-oxopiperidine-1,3-dicarboxylateAusbeute 38,2 %

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 4-oxo-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester (73.36 g, 0.27 mol) in DMF (734 mL) lithium carbonate (50 g, 0.676 mol) was added, followed by benzyl bromide (55.44 g, 0.324 mol). The mixture was heated to about 60° C. and stirred for about 20 hours. The reaction mixture was then cooled to room temperature and extracted with IPE, washed with water and dried over magnesium sulfate. After filtration and concentration in vacuo a solid was obtained. Recrystallization of the crude product in hexane afforded a white solid (33.6 g, yield 38.2%).

Aufarbeitung

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. extractionextracted with IPE
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationAfter filtration and concentration in vacuo a solid
  6. customwas obtained
  7. customRecrystallization of the crude product in hexane

Quellen und Nachweise

ORD-Eintrag
ord-ccb76594ddb642d3bb1bd93a43408cbe
Quelldatensatz
uspto-grants-2002_09
Patentnummer
US06448263B1

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