Water → HCID 68406269, Verbindung

HRID 43936

Reaktionsgleichung

Reaktionsgleichung von HRID 43936
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:27](I)[CH2:28][CH3:29].O>C1COCC1>[C:1]([O:5][C:6]([N:8]([CH2:27][CH2:28][CH3:29])[CH:9]1[CH2:10][CH2:11][N:12]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH2:13][CH2:14]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydride2×HCID 336431-Iodopropane2×HCID 21981786Benzyl 4-((tert-butoxycarbonyl)amino)piperidine-1-carboxylate

Produkt 1

HCID 68406269HCID 68406269, VerbindungAusbeute 26,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of benzyl 4-[(tert-butoxycarbonyl)amino]piperidine-1-carboxylate obtained in Example (241a) (1.00 g, 2.99 mmol) in THF (5 mL) was added to a suspension of sodium hydride (55%) (261 mg, 5.98 mmol) in THF (25 mL) at 0° C. Subsequently, propyl iodide (1.46 mL, 15.0 mmol) was added at 0° C., and the mixture was stirred at room temperature for 22 hours. Thereafter, sodium hydride (55%) (130 mg, 2.99 mmol) and propyl iodide (0.58 mL, 5.98 mmol) were added, and the mixture was heated under reflux for 22 hours. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. Thereafter, the combined organic layers were washed with brine and dried over anhydrous magnesium sulfate. Following filtration, the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=5/1) to obtain 301 mg of the title compound as a pale yellow oily substance (27%).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 22 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThereafter, the combined organic layers were washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltration
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe resulting residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=5/1)

Quellen und Nachweise

ORD-Eintrag
ord-62988030973a43508cfc013c231c063f
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536197B2

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