Methyl 5-(benzoyloxy-carbonyl)-2,4-dimethyl-3-pyrrolepropionate → Methyl 2,4-dimethyl-3-pyrrolepropionate

HRID 2381250Notes

Reaction equation

HRID 2381250 reaction equation
C(OC([C:12]1[NH:16][C:15]([CH3:17])=[C:14]([CH2:18][CH2:19][C:20]([O:22][CH3:23])=[O:21])[C:13]=1[CH3:24])=O)(=O)C1C=CC=CC=1>CC(C)=O.[Pd]>[CH3:17][C:15]1[NH:16][CH:12]=[C:13]([CH3:24])[C:14]=1[CH2:18][CH2:19][C:20]([O:22][CH3:23])=[O:21]

Participants

4

Reactant 1

HCID 86639973Methyl 5-(benzoyloxy-carbonyl)-2,4-dimethyl-3-pyrrolepropionate

Product 1

HCID 10559312Methyl 2,4-dimethyl-3-pyrrolepropionate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 180AcetoneSolvent

Procedure

Methyl 5-(benzoyloxy-carbonyl)-2,4-dimethyl-3-pyrrolepropionate (1.55 g, 4.91 mmol) was dissolved in acetone (150 mL) containing 10% palladium/carbon, and the mixture was stirred at room temperature for 12 hours under a hydrogen atmosphere. The reaction mixture was filtered, the solvent was evaporated under reduced pressure, then the residue was immediately dissolved in trifluoroacetic acid (TFA, 10 mL), and the mixture was stirred at room temperature for 10 minutes under an argon atmosphere. The reaction mixture was added with dichloromethane (30 mL), then washed successively with water and 1 mol/L aqueous sodium hydrogencarbonate, dried over anhydrous sodium sulfate, and evaporated under reduced pressure to obtain pale brown oil (1, 0.835 g, 94%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe solvent was evaporated under reduced pressure
  3. dissolutionthe residue was immediately dissolved in trifluoroacetic acid (TFA, 10 mL)
  4. stirringthe mixture was stirred at room temperature for 10 minutes under an argon atmosphere
  5. additionThe reaction mixture was added with dichloromethane (30 mL)
  6. washwashed successively with water and 1 mol/L aqueous sodium hydrogencarbonate
  7. dry with materialdried over anhydrous sodium sulfate
  8. customevaporated under reduced pressure
  9. customto obtain pale brown oil (1, 0.835 g, 94%)

Sources & evidence

ORD record
ord-39cc9f3e0dae437a8e596f91286f3471
Source dataset
uspto-grants-2012_09
Patent number
US08258171B2

Reaction notes

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