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Methyl iodide → 1-Benzyl 3-ethyl 3-methylpiperidine-1,3-dicarboxylate

HRID 408227
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 408227
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[N:11]1([C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:23])[CH2:16][CH2:15][CH2:14][CH:13]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:12]1.[CH3:32]I.[Cl-].[NH4+]>C1COCC1>[CH3:32][C:13]1([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:14][CH2:15][CH2:16][N:11]([C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:23])[CH2:12]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 2733832Lithium hexamethyldisilazaneHCID 17999271Benzyl ethyl piperidine-1,3-dicarboxylate

Produkt 1

HCID 534862661-Benzyl 3-ethyl 3-methylpiperidine-1,3-dicarboxylateAusbeute 98,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

Lithium bis(trimethylsilyl)amide (12.9 mL, 12.9 mmol, 1M solution in THF) at −78° C. was added to 1-benzyl 3-ethyl piperidine-1,3-dicarboxylate (3.0 g, 10.3 mmol) in THF (20 mL), and the reaction was stirred at this temperature for 20 minutes. MeI (0.867 mL, 13.9 mmol) was added, and the reaction was warmed to room temperature. After 2 hours at room temperature, the mixture was poured onto saturated ammonium chloride (20 mL) and extracted with ether, washed with brine and dried over sodium sulfate. After removal of the solvent, the residue was purified by chromatography on silica gel (hexane:ethyl acetate, 5:1) to give 1-benzyl 3-ethyl 3-methylpiperidine-1,3-dicarboxylate (3.1 g, 98% yield) as an oil.

Aufarbeitung

  1. waitAfter 2 hours at room temperature
  2. extractionextracted with ether
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. customAfter removal of the solvent
  6. customthe residue was purified by chromatography on silica gel (hexane:ethyl acetate, 5:1)

Quellen und Nachweise

ORD-Eintrag
ord-6cac3eade4724b3b840ea65a8017da14
Quelldatensatz
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08758830B2

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