Methanol → 5-Benzoyl-7-bromo-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid

HRID 2164651Notes

Reaction equation

HRID 2164651 reaction equation
[C:1]([C:9]1[N:13]2[CH2:14][CH2:15][CH:16]([C:17]([O:19]C(C)C)=[O:18])[C:12]2=[C:11]([Br:23])[CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.C(=O)([O-])[O-].[K+].[K+]>O>[C:1]([C:9]1[N:13]2[CH2:14][CH2:15][CH:16]([C:17]([OH:19])=[O:18])[C:12]2=[C:11]([Br:23])[CH:10]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 20404966isopropyl 5-benzoyl-7-bromo-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylate

Product 1

HCID 155806305-Benzoyl-7-bromo-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 336 mg. of isopropyl 5-benzoyl-7-bromo-1,2-dihydro-3H-pyrrolo[1,2-a]-pyrrole-1-carboxylate in 10 ml. of methanol is treated with a solution of 690 mg. of potassium carbonate in 5 ml. of water. The reaction mixture is refluxed under nitrogen atmosphere for 30 minutes, cooled, and evaporated to dryness. The residue is taken up in 10 ml. of 10% aqueous hydrochloric acid and 50 ml. of water and the resultant mixture extracted with ethyl acetate (2×50 ml.). The combined extracts are dried over magnesium sulfate and evaporated to dryness under reduced pressure. Crystallization of the residue from ethyl acetate-hexane affords 5-benzoyl-7-bromo-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid.

Workup

  1. temperatureThe reaction mixture is refluxed under nitrogen atmosphere for 30 minutes
  2. temperaturecooled
  3. customevaporated to dryness
  4. extractionof water and the resultant mixture extracted with ethyl acetate (2×50 ml.)
  5. dry with materialThe combined extracts are dried over magnesium sulfate
  6. customevaporated to dryness under reduced pressure
  7. customCrystallization of the residue from ethyl acetate-hexane

Sources & evidence

ORD record
ord-7eaf5268d43349e9af39871638608ec0
Source dataset
uspto-grants-1985_03
Patent number
US04505927

Reaction notes

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