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

HRID 980454Notes

Reaction equation

HRID 980454 reaction equation
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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-4308614fb8ec4a1582666640fb91b8e6
Source dataset
uspto-grants-1987_01
Patent number
US04638006

Reaction notes

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