Methanol → 5-Benzoyl-7-bromo-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid
Reaction equation
[C:1]([C:9]1[N:13]2[CH2:14][CH2:15][CH:16]([C:17]([O:19]CC)=[O:18])[C:12]2=[C:11]([Br:22])[CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.[OH-].[Na+]>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:22])[CH:10]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
Procedure
A solution of 250 mg. of ethyl 5-benzoyl-7-bromo-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylate in 8 ml. of methanol is treated under an atmosphere of nitrogen, with a solution of 200 mg. of sodium hydroxide in 1 ml. of water, maintaining the reaction mixture at room temperature for 1.5 hours. The methanol is then removed under reduced pressure and the basic solution which remains is diluted with 5 ml. of water and extracted with ether to remove any unsaponifiable product. The aqueous solution is acidified with 10% hydrochloric acid and extracted three times with ethyl acetate. The combined extracts are dried and evaporated to dryness under reduced pressure, and the residue crystallized from ethyl acetate-hexane, to give 5-benzoyl-7-bromo-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid.
Workup
- customThe methanol is then removed under reduced pressure
- additionthe basic solution which remains is diluted with 5 ml
- extractionof water and extracted with ether
- customto remove any unsaponifiable product
- extractionextracted three times with ethyl acetate
- customThe combined extracts are dried
- customevaporated to dryness under reduced pressure
- customthe residue crystallized from ethyl acetate-hexane
Sources & evidence
- ORD record
- ord-f9d0852d2d9e4d53a18ed58cdae92a40
- Source dataset
- uspto-grants-1982_08
- Patent number
- US04347185
Reaction notes
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