diethyl 5-benzoyl-2,3-dihydro-1H-pyrrolizine-1,1-dicarboxylate → Ketorolac

HRID 1090819Notes

Reaction equation

HRID 1090819 reaction equation
[C:1]([C:9]1[N:10]2[C:14](=[CH:15][CH:16]=1)[C:13](C(OCC)=O)([C:17]([O:19]CC)=[O:18])[CH2:12][CH2:11]2)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(OCC)C.[OH-].[Na+]>[C:1]([C:9]1[N:10]2[C:14](=[CH:15][CH:16]=1)[CH:13]([C:17]([OH:19])=[O:18])[CH2:12][CH2:11]2)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 9928574diethyl 5-benzoyl-2,3-dihydro-1H-pyrrolizine-1,1-dicarboxylate

Product 1

HCID 3826KetorolacYield 93%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of diethyl 5-benzoyl-2,3-dihydro-1H-pyrrolizine-1,1-dicarboxylate (600 mg, I.69 mmol) in diethyl ether and 20% aqueous sodium hydroxide (10 mL) was refluxed with vigorous stirring for 24 hours. The aqueous layer was washed with ether (20 mL), and acidified with concentrated hydrochloric acid. The aqueous layer was washed with ethyl acetate (3×20 mL). The ethyl acetate extracts were combined and warmed at 70° C. for 4 hours. The ethyl acetate solution was concentrated under reduced pressure to yield 400 mg (93%) of 5-benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid as a pure solid.

Workup

  1. temperaturewas refluxed
  2. washThe aqueous layer was washed with ether (20 mL)
  3. washThe aqueous layer was washed with ethyl acetate (3×20 mL)
  4. concentrationThe ethyl acetate solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-106c8dffeeff45768a0a4827fee39142
Source dataset
uspto-grants-1992_01
Patent number
US05082950

Reaction notes

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