2-Benzyloxycarbonylmethyl-2-(pyrrol-1-yl)malonic acid diethyl ester → 2-Carboxymethyl-2-(pyrrol-1-yl)-malonic acid diethyl ester

HRID 256583Notes

Reaction equation

HRID 256583 reaction equation
[CH2:1]([O:3][C:4](=[O:27])[C:5]([CH2:16][C:17]([O:19]CC1C=CC=CC=1)=[O:18])([N:11]1[CH:15]=[CH:14][CH:13]=[CH:12]1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2]>O1CCOCC1.[C].[Pd]>[CH2:1]([O:3][C:4](=[O:27])[C:5]([CH2:16][C:17]([OH:19])=[O:18])([N:11]1[CH:12]=[CH:13][CH:14]=[CH:15]1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2]

Participants

4

Reactant 1

HCID 106193402-Benzyloxycarbonylmethyl-2-(pyrrol-1-yl)malonic acid diethyl ester

Product 1

HCID 108029052-Carboxymethyl-2-(pyrrol-1-yl)-malonic acid diethyl esterYield 80.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-benzyloxycarbonylmethyl-2-(pyrrol-1-yl)malonic acid diethyl ester (80.0 g) in dioxane (150 ml) was hydrogenated over 10% palladium-carbon (500 mg) at 40° C. After the calculated amount of hydrogen was absorbed, the catalyst was filtered off and the filtrate was evaporated under reduced pressure. The residue was recrystallized from ethyl acetate/n-hexane to give the title compound (48.7 g, 80.2%) as colorless crystals, mp 93°-94° C.

Workup

  1. customAfter the calculated amount of hydrogen was absorbed
  2. filtrationthe catalyst was filtered off
  3. customthe filtrate was evaporated under reduced pressure
  4. customThe residue was recrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-aaf7310e824b4202a08add87a34cb156
Source dataset
uspto-grants-1993_11
Patent number
US05258382

Reaction notes

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