Pyridine → Ethyl 4-(1-benzyloxycarbonyl-4-piperidyl)-2-chlorobutyrate

HRID 464879Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 464879
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][CH:19](O)[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.S(Cl)([Cl:34])=O>O.C(OCC)(=O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][CH:19]([Cl:34])[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 20143718Ethyl 4-(1-benzyloxycarbonyl-4-piperidyl)-2-hydroxybutyrate

Produkt 1

HCID 20143712Ethyl 4-(1-benzyloxycarbonyl-4-piperidyl)-2-chlorobutyrate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

To a mixture of ethyl 4-(1-benzyloxycarbonyl-4-piperidyl)-2-hydroxybutyrate (11.5 g), ethyl acetate (200 ml) and pyridine (12 g) is added thionyl chloride (5 ml), and the resulting mixture is refluxed for 1 hour with stirring. After cooling, the mixture is diluted with water (500 ml) and ethyl acetate (100 ml). The organic layer is separated, washed successively with 0.1N hydrochloric acid and water, dried over anhydrous magnesium sulfate, treated with activated carbon and then evaporated in vacuo to give ethyl 4-(1-benzyloxycarbonyl-4-piperidyl)-2-chlorobutyrate (10.5 g) as a pale yellow oil.

Aufarbeitung

  1. temperaturethe resulting mixture is refluxed for 1 hour
  2. temperatureAfter cooling
  3. customThe organic layer is separated
  4. washwashed successively with 0.1N hydrochloric acid and water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. additiontreated with activated carbon
  7. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-dbf18d7bdabb464dbb17c80e21d0722a
Quelldatensatz
uspto-grants-1985_10
Patentnummer
US04548932

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