Benzyl 4-carboxy-1-(3,4-dichlorobenzyl)cyclopenta[b]pyrrole-2-carboxylate → 1-(3,4-Dichlorobenzyl)cyclopenta[b]pyrrole-2,4-dicarboxylic Acid

HRID 1596540Notes

Reaction equation

HRID 1596540 reaction equation
[C:1]([C:4]1[C:11]2[C:7]([N:8]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([Cl:30])[CH:24]=3)[CH:9]([C:12]([O:14]CC3C=CC=CC=3)=[O:13])[CH:10]=2)=[CH:6][CH:5]=1)([OH:3])=[O:2].[H][H]>C(OCC)(=O)C.[Pd].[OH-].[Na+].O>[Cl:30][C:25]1[CH:24]=[C:23]([CH:28]=[CH:27][C:26]=1[Cl:29])[CH2:22][N:8]1[CH:9]([C:12]([OH:14])=[O:13])[CH:10]=[C:11]2[C:4]([C:1]([OH:3])=[O:2])=[CH:5][CH:6]=[C:7]12

Participants

7

Reactant 2

HCID 21702192Benzyl 4-carboxy-1-(3,4-dichlorobenzyl)cyclopenta[b]pyrrole-2-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 217021861-(3,4-Dichlorobenzyl)cyclopenta[b]pyrrole-2,4-dicarboxylic AcidYield 41%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Procedure

Benzyl 4-carboxy-1-(3,4-dichlorobenzyl)cyclopenta[b]pyrrole-2-carboxylate (0.1 g) was dissolved in ethyl acetate (5 mL). Palladium on carbon (5% Pd, 10 mg) was added and the reaction was exposed to an hydrogen atmosphere (1.1 atm) for 4 hours until reaction was complete. The hydrogen was evacuated and the resulting solution was filtered through Celite to remove catalyst. The reaction was concentrated in vacuo to afford the crude product, which was dissolved in a minimum of 2M NaOH, diluted with water (1 mL), and then precipitated by addition of dilute aqueous HCl. The solid was collected and dried to yield the title product as a pale cream solid (32 mg, 41%), NMR d(DMSO) 2.40 (4H, m), 3.70 (1H, t), 5.40 (2H, AB d), 6.68 (1H, s), 6.95 (1H, dd), 7.15 (1H, s), 7.58 (1H, d); M/z (−) 355, 353 (MH+).

Workup

  1. customThe hydrogen was evacuated
  2. filtrationthe resulting solution was filtered through Celite
  3. customto remove catalyst
  4. concentrationThe reaction was concentrated in vacuo
  5. customto afford the crude product, which
  6. customprecipitated by addition of dilute aqueous HCl
  7. customThe solid was collected
  8. customdried

Sources & evidence

ORD record
ord-92627f16d3c74f9782b448c24e63b249
Source dataset
uspto-grants-2001_09
Patent number
US06291507B1

Reaction notes

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