Acetic Acid → Ethyl 4-(1-benzyloxycarbonyl-4-piperidyl)-2-hydroxybutyrate

HRID 980604Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 980604
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][C:19](=[O:25])[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.C(O)(=O)C.C([BH3-])#N.[Na+].O>C(O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][CH:19]([OH:25])[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 962WaterHCID 5003444Sodium cyanoborohydrideHCID 19868897Ethyl 4-(1-benzyloxycarbonyl-4-piperidyl)-2-oxobutyrate

Produkt 1

HCID 20143718Ethyl 4-(1-benzyloxycarbonyl-4-piperidyl)-2-hydroxybutyrateAusbeute 67,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

In 30 ml of ethanol is dissolved 17 g of ethyl 4-(1-benzyloxycarbonyl-4-piperidyl)-2-oxobutyrate, and 4.5 g of acetic acid is added to the solution. Sodium cyanoborohydride (3 g) is added to the mixture at room temperature with stirring, followed by stirring at room temperature for 3 hours, and 500 ml of water is added to the reaction mixture, which is extracted with methylene chloride. The extract is dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and the resulting residue is purified by silica-gel column chromatography (hexane:ethyl acetate=2:1 to 1:1) to give 11.5 g of ethyl 4-(1-benzyloxycarbonyl-4-piperidyl)-2-hydroxybutyrate as a colorless oily material.

Aufarbeitung

  1. additionis added to the solution
  2. stirringby stirring at room temperature for 3 hours
  3. extractionis extracted with methylene chloride
  4. dry with materialThe extract is dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customthe resulting residue is purified by silica-gel column chromatography (hexane:ethyl acetate=2:1 to 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-dda132f23b6c484499db454e585b69f6
Quelldatensatz
uspto-grants-1987_01
Patentnummer
US04638000

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