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

HRID 2120256Notes

Reaction equation

HRID 2120256 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>[Pd].CO>[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])([OH:10])=[O:8]

Participants

4

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 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2-Benzyloxycarbonyl-3,5-dimethyl-4-(2-methoxycarbonylethyl)pyrrole (Aldrich, 2.0 g) was hydrogenated over 0.2 g of 10% palladium on carbon in 40 mL of methanol for 2 hours at room temperature. The catalyst was removed by filtration and washed with 40 mL of methanol. The filtrate was evaporated to dryness and dried overnight in a vacuum oven to give 1.3 g (92% yield) of 2-carboxy-3,5-dimethyl-4-(2-methoxycarbonylethyl)pyrrole.

Workup

  1. customThe catalyst was removed by filtration
  2. washwashed with 40 mL of methanol
  3. customThe filtrate was evaporated to dryness
  4. customdried overnight in a vacuum oven

Sources & evidence

ORD record
ord-b4414bd282044e09982bfadad71d1f1d
Source dataset
uspto-grants-2004_02
Patent number
US06689806B1

Reaction notes

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