Methyl 5-(benzyloxycarbonyl)-2,4-dimethyl-3-pyrrolepropionate → 4-(2-METHOXYCARBONYL-ETHYL)-3,5-DIMETHYL-1H-PYRROLE-2-CARBOXYLIC ACID

HRID 2375791Notes

Reaction equation

HRID 2375791 reaction equation
C([O:8][C:9]([C:11]1[NH:12][C:13]([CH3:23])=[C:14]([CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])[C:15]=1[CH3:16])=[O:10])C1C=CC=CC=1>CO>[CH3:22][O:21][C:19]([CH2:18][CH2:17][C:14]1[C:15]([CH3:16])=[C:11]([C:9]([OH:10])=[O:8])[NH:12][C:13]=1[CH3:23])=[O:20]

Participants

3

Reactant 1

HCID 657433Methyl 5-(benzyloxycarbonyl)-2,4-dimethyl-3-pyrrolepropionate

Product 1

HCID 108468134-(2-METHOXYCARBONYL-ETHYL)-3,5-DIMETHYL-1H-PYRROLE-2-CARBOXYLIC ACIDYield 94.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-(2-methoxycarbonyl-ethyl)-3,5-dimethyl-1H-pyrrole-2-carboxylic acid benzyl ester (390 mg, 1.24 mmol) was dissolved in anhydrous MeOH (20 mL). The solution was evacuated and rinsed with argon several times. 120 mg of palladium on charcoal (10%) were added and again the mixture was evacuated and rinsed with argon several times. Finally argon was exchanged by hydrogen (balloon filled with hydrogen) and the mixture was stirred for 3 h at room temperature. The reaction mixture was filtered over celite and the filter residue was washed with MeOH (150 mL). The filtrate was concentrated in vacuo to give pure 4-(2-methoxycarbonyl-ethyl)-3,5-dimethyl-1H-pyrrole-2-carboxylic acid as a colorless solid (263 mg). MS (ESI−): m/e=225 [M−H]−.

Workup

  1. customThe solution was evacuated
  2. washrinsed with argon several times
  3. addition120 mg of palladium on charcoal (10%) were added
  4. customagain the mixture was evacuated
  5. washrinsed with argon several times
  6. filtrationThe reaction mixture was filtered over celite
  7. washthe filter residue was washed with MeOH (150 mL)
  8. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-7cc4a382463d4dd3b14bb8fd89fd3053
Source dataset
uspto-grants-2008_12
Patent number
US07465806B2

Reaction notes

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