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Methyl iodide → HCID 68005624, Verbindung

HRID 1026553
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1026553
O1CCC[CH2:2]1.[Cl:6][C:7]1[CH:16]=[C:15]2[C:10]([CH2:11][CH2:12][C:13](=[O:30])[N:14]2[CH:17]2[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]2)=[N:9][CH:8]=1.C[Si](C)(C)[N-][Si](C)(C)C.[Li+].CI>O.C(OCC)(=O)C>[Cl:6][C:7]1[CH:16]=[C:15]2[C:10]([CH2:11][CH:12]([CH3:2])[C:13](=[O:30])[N:14]2[CH:17]2[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:27])([CH3:29])[CH3:28])=[O:24])[CH2:19][CH2:18]2)=[N:9][CH:8]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 6328Methyl iodideHCID 8028Tetrahydrofuran3×HCID 2733832Lithium hexamethyldisilazaneHCID 68006101HCID 68006101, Verbindung

Produkt 1

HCID 68005624HCID 68005624, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962
Water
Lösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a tetrahydrofuran solution (195 ml) of tert-butyl 4-(7-chloro-2-oxo-3,4-dihydro-1,5-naphthyridin-1(2H)-yl)piperidine-1-carboxylate (13.0 g) was added dropwise at −78° C. a tetrahydrofuran solution (1 M, 39.1 ml) of lithium hexamethyldisilazide. After stirring at the same temperature for 30 minutes, a tetrahydrofuran solution (65 ml) of methyl iodide (2.65 ml) was added dropwise. After stirring at the same temperature for 10 minutes and under ice cooling for 1 hour, ethyl acetate and water were added to the reaction solution, and the solution was separated. The organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to afford tert-butyl 4-(7-chloro-3-methyl-2-oxo-3,4-dihydro-1,5-naphthyridin-1(2H)-yl)piperidine-1-carboxylate (12.2 g).

Aufarbeitung

  1. stirringAfter stirring at the same temperature for 10 minutes and under ice cooling for 1 hour
  2. customthe solution was separated
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-538353eeb79d40d081f494d9a295ff8f
Quelldatensatz
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08729095B2

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