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Trifluoroacetic acid → 2-(1-Benzyl-pyrrolidin-3-yl)-5-nitro-pyridine

HRID 2262605
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2262605
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH:10]=[CH2:11])=[N:8][CH:9]=1)([O-:3])=[O:2].FC(F)(F)C(O)=O.[CH2:19]([N:26]([CH2:32]OC)[CH2:27][Si](C)(C)C)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>ClCCl>[CH2:19]([N:26]1[CH2:32][CH2:11][CH:10]([C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][N:8]=2)[CH2:27]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 230905502-Ethenyl-5-nitropyridine

Produkt 1

HCID 574700722-(1-Benzyl-pyrrolidin-3-yl)-5-nitro-pyridineAusbeute 65,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

0.15 g of 5-nitro-2-vinyl-pyridine were dissolved in 2.5 ml of dichloromethane, 0.149 g of trifluoroacetic acid (1.31 mmol) were added, followed by slow addition of 0.928 g of N-benzyl-N-(methoxymethyl)-N-trimethylsilylmethylamine (3.91 mmol). Stirring was continued at room temperature for 1 h, before the reaction mixture was washed with aqueous sodium hydrogencarbonate, the aqueous layer reextracted with dichloromethane, the organic layers combined, dried over magnesium sulfate, filtered, and the solvent evaporated under reduced pressure. The crude product was purified via silica gel chromatography with ethyl acetate. Fractions containing the product were combined, the solvent evaporated to yield 0.186 g of the desired product.

Aufarbeitung

  1. washwas washed with aqueous sodium hydrogencarbonate
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customthe solvent evaporated under reduced pressure
  5. customThe crude product was purified via silica gel chromatography with ethyl acetate
  6. additionFractions containing the product
  7. customthe solvent evaporated

Quellen und Nachweise

ORD-Eintrag
ord-0249cf4f1e534889a8f4ee958bfa8a2c
Quelldatensatz
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07851463B2

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