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Methyl iodide → HCID 71268626, Verbindung

HRID 70780
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 70780
[H-].[Na+].[CH2:3]([O:10][CH2:11][C:12]1([OH:25])[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:26]I.[Cl-].[NH4+]>CCOC(C)=O.CN(C=O)C>[CH2:3]([O:10][CH2:11][C:12]1([O:25][CH3:26])[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:22])([CH3:24])[CH3:23])=[O:19])[CH2:14][CH2:13]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 71268665HCID 71268665, Verbindung

Produkt 1

HCID 71268626HCID 71268626, VerbindungAusbeute 89,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228
Dimethylformamide
Lösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

55% sodium hydride (4.06 g) was added under ice-cooling to a DMF (100 ml) solution of tert-butyl 4-[(benzyloxy)methyl]-4-hydroxypiperidine-1-carboxylate (9.96 g), and stirring was performed at 50° C. for 40 minutes. Under ice-cooling, methyl iodide (22.0 g) was added dropwise, and the mixture was stirred at room temperature for 4 hours. After adding a saturated ammonium chloride aqueous solution and purified water to the reaction liquid, extraction was performed with EtOAc. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (EtOAc/hexane) to obtain tert-butyl 4-[(benzyloxy)methyl]-4-methoxypiperidine-1-carboxylate (9.27 g).

Aufarbeitung

  1. temperatureUnder ice-cooling
  2. stirringthe mixture was stirred at room temperature for 4 hours
  3. custompurified water
  4. customto the reaction liquid, extraction
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue was purified by silica gel column chromatography (EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-5f9b8ad339bb4a6fa06d0c1a90bb1a22
Quelldatensatz
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08822688B2

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