Acetone → 5-oxo-hexahydro-1H-pyrrolizine-3-carboxylic acid

HRID 980454Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 980454
C([O:3][C:4]([CH:6]1[N:13]2[CH:9]([CH2:10][CH2:11][C:12]2=[O:14])[CH2:8][CH2:7]1)=[O:5])C.[OH-].[Na+].CC(C)=O>C(O)C>[O:14]=[C:12]1[CH2:11][CH2:10][CH:9]2[N:13]1[CH:6]([C:4]([OH:5])=[O:3])[CH2:7][CH2:8]2

Komponenten

5

Edukt 3

HCID 180AcetoneHCID 14798Sodium HydroxideHCID 13756031hexahydro-5-oxo-1H-pyrrolizine-3-carboxylic acid ethyl ester

Produkt 1

HCID 137560335-oxo-hexahydro-1H-pyrrolizine-3-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of hexahydro-5-oxo-1H-pyrrolizine 3-carboxylic acid ethyl ester (12.6 g, 0.064 mol) in ethanol (35 ml) is treated with a 2N sodium hydroxide solution (35 ml, 0.07 mol) with stirring for 72 hours. The solution is concentrated at reduced pressure and treated with concentrated hydrochloric acid (6 ml) dropwise. The solution is extracted with dichloromethane. The extracts are dried (MgSO4), filtered, and concentrated to yield an oil. Trituration of the oil with acetone yields hexahydro-5-oxo-1H-pyrrolizine 3-carboxylic acid as a white solid with mp 145°-148° C.

Aufarbeitung

  1. concentrationThe solution is concentrated at reduced pressure
  2. additiontreated with concentrated hydrochloric acid (6 ml) dropwise
  3. extractionThe solution is extracted with dichloromethane
  4. dry with materialThe extracts are dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto yield an oil

Quellen und Nachweise

ORD-Eintrag
ord-4308614fb8ec4a1582666640fb91b8e6
Quelldatensatz
uspto-grants-1987_01
Patentnummer
US04638006

Notizen zur Reaktion

Wird geladen…