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Pyridine → 2,3-Bis(1,1-dimethylethyl) 1-(2-propen-1-yl) 1,2,3-pyrazolidinetricarboxylate

HRID 1396913
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1396913
Cl[C:2]([O:4][CH2:5][CH:6]=[CH2:7])=[O:3].[N:8]1([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH:12]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:11][CH2:10][NH:9]1.N1C=CC=CC=1>O1CCCC1>[N:9]1([C:2]([O:4][CH2:5][CH:6]=[CH2:7])=[O:3])[CH2:10][CH2:11][CH:12]([C:13]([O:15][C:16]([CH3:18])([CH3:19])[CH3:17])=[O:14])[N:8]1[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 18052Allyl chloroformateHCID 68287714Di-tert-butyl pyrazolidine-1,5-dicarboxylate

Produkt 1

HCID 867063572,3-Bis(1,1-dimethylethyl) 1-(2-propen-1-yl) 1,2,3-pyrazolidinetricarboxylateAusbeute 57,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Allyl chloroformate (0.488 ml, 4.59 mmol) was added dropwise to the solution of di-tert-butyl pyrazolidine-1,5-dicarboxylate (1 g, 3.67 mmol) and pyridine (0.371 ml, 4.59 mmol) in tetrahydrofuran (THF) (1.79 ml) at 0° C. The resulting solution was allowed to warm up to ambient temperature and stirred for 30 min. The reaction was filtered, and to the filtrate was added EtOAc. The solution was washed with brine. The organic layers were separated and dried over anhydrous Na2SO4. The crude product was purified by RP-HPLC to give 2,3-bis(1,1-dimethylethyl) 1-(2-propen-1-yl) 1,2,3-pyrazolidinetricarboxylate (749 mg, 2.101 mmol, 57% yield). MS (ES+) m/z 357.3 (MH+).

Aufarbeitung

  1. filtrationThe reaction was filtered
  2. additionto the filtrate was added EtOAc
  3. washThe solution was washed with brine
  4. customThe organic layers were separated
  5. dry with materialdried over anhydrous Na2SO4
  6. customThe crude product was purified by RP-HPLC

Quellen und Nachweise

ORD-Eintrag
ord-cecc4d4c1ee84a3cb657f2259970bd9c
Quelldatensatz
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08901119B2

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