Water → Benzyl 4-methoxypiperidine-1-carboxylate

HRID 253060

Reaktionsgleichung

Reaktionsgleichung von HRID 253060
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([OH:17])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:20]I.O>CN(C)C=O.C(OCC)(=O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([O:17][CH3:20])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 2794620Benzyl 4-Hydroxy-1-piperidinecarboxylate

Produkt 1

HCID 23024301Benzyl 4-methoxypiperidine-1-carboxylateAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 1-benzyloxycarbonyl-4-hydroxypiperidine (1.3 g) in dimethylformamide (10 mL) was added sodium hydride (360 mL) under ice cooling and the mixture was stirred at room temperature under nitrogen-gas atmosphere for 1 hours. To the reaction mixture was added methyl iodide (374 μL) under ice-cooling and the mixture was stirred at the same temperature for 1 hour and at room temperature for 2 hours. To the reaction mixture was added water and ethyl acetate and the mixture was stirred. The organic layer washed with a brine, dried over magnesium sulfate and filtered. The filtrate was concentrated in vacuo and the resultant crude product was purified by column chromatography on silica gel (solvent: hexane/ethyl acetate=88/12 to 70/30) to obtain 1-benzyloxycarbonyl-4-methoxypiperidine (622 mg, yield: 45%) as a pale yellow oil.

Aufarbeitung

  1. temperaturecooling
  2. stirringthe mixture was stirred at the same temperature for 1 hour and at room temperature for 2 hours
  3. stirringthe mixture was stirred
  4. washThe organic layer washed with a brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated in vacuo
  8. customthe resultant crude product was purified by column chromatography on silica gel (solvent: hexane/ethyl acetate=88/12 to 70/30)

Quellen und Nachweise

ORD-Eintrag
ord-e9dd1c0189ef49e99991622f5a437a99
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07872006B2

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