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

HRID 67889Notes

Reaction equation

HRID 67889 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 minitres, 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 minitres
  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-4d0cc944adab44b2ab2aa844f16512e8
Source dataset
uspto-grants-1982_08
Patent number
US04347185

Reaction notes

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