Trifluoroacetic acid → Ketorolac

HRID 2413347Notes

Reaction equation

HRID 2413347 reaction equation
[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](C(O)=O)[CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>>[C:1]([C:9]1[N:13]2[CH2:14][CH2:15][CH:16]([C:17]([OH:19])=[O:18])[C:12]2=[CH:11][CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 204308795-Benzoyl-2,3-dihydro-1H-pyrrolizine-1,7-dicarboxylic acid

Product 1

HCID 3826Ketorolac

Procedure

The acidic decarboxylation is conducted under mild conditions. For example, 5-benzoyl-7-hydroxycarbonyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-caboxylic acid is treated with refluxing trifluoroacetic acid to afford 5-benzoyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid. Other acids may also be used. For example, those listed below in Table I.

Sources & evidence

ORD record
ord-23dad51471844ccdbd0ea3b2bf6f706e
Source dataset
uspto-grants-1985_01
Patent number
US04496741

Reaction notes

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