Bromide ion → Benzyl 4-methylidenepiperidine-1-carboxylate

HRID 47307

Reaktionsgleichung

Reaktionsgleichung von HRID 47307
[Br-].[C:2](O[K])([CH3:5])([CH3:4])[CH3:3].O=C1C[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]C1>O1CCCC1>[CH2:3]=[C:2]1[CH2:5][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][CH2:4]1

Komponenten

5

Edukt 3

HCID 259Bromide ionHCID 643496Benzyl 4-oxopiperidine-1-carboxylateHCID 178418922HCID 178418922, Verbindung

Produkt 1

HCID 15519136Benzyl 4-methylidenepiperidine-1-carboxylateAusbeute 159,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

51.1 g of methyltoluphenylphosphonium bromide was added to a mixture of 16.1 g tert-butoxy potassium and 500 ml tetrahydrofuran, and then stirred for 1 hr and 20 min at room temperature. 16.1 g of benzyl 4-oxo-1-piperidinecarboxylate was added thereto, and the mixture was stirred for 2 hr and 40 min at room temperature. The reaction solution was evaporated, diethyl ether was added thereto, and then filtered through Celite. The filtrate was washed with water and brine, dried over anhydrous magnesium sulfate, and then filtered. The filtrate was evaporated, and the resulting residue was subjected to silica gel-column chromatography to give 25.5 g of benzyl 4-methylene-1-piperidinecarboxylate.

Aufarbeitung

  1. stirringthe mixture was stirred for 2 hr and 40 min at room temperature
  2. customThe reaction solution was evaporated
  3. additiondiethyl ether was added
  4. filtrationfiltered through Celite
  5. washThe filtrate was washed with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customThe filtrate was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-28f15de1c3324835b374d20f7606c6c9
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06699870B2

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