Benzyl 3-(1-methyl-3-pyrrolecarboxamido)propionate → HCID 10821710, compound

HRID 1595158Notes

Reaction equation

HRID 1595158 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([C:7]([NH:9][CH2:10][CH2:11][C:12]([O:14]CC2C=CC=CC=2)=[O:13])=[O:8])=[CH:3]1>O1CCCC1.[Pd]>[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([C:7]([NH:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[O:8])=[CH:3]1

Participants

4

Reactant 1

HCID 10803123Benzyl 3-(1-methyl-3-pyrrolecarboxamido)propionate

Product 1

HCID 10821710HCID 10821710, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

5%-palladium/carbon (716 mg) was added to a solution of Compound 3 (7.16 g, 25 mmole) in tetrahydrofuran (hereinafter called “THF”) (300 ml), followed by stirring for 72 hours under a hydrogen gas stream. The reaction mixture was filtered, and the solid was washed with methanol. The filtrate and the washing were combined, followed by concentration under reduced pressure. The residue was recrystallized from acetonitrile, whereby the title compound (4.14 g) was obtained (yield: 84%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe solid was washed with methanol
  3. concentrationfollowed by concentration under reduced pressure
  4. customThe residue was recrystallized from acetonitrile, whereby the title compound (4.14 g)
  5. customwas obtained (yield: 84%)

Sources & evidence

ORD record
ord-8f66cd71d6b84783a9339bfe86960987
Source dataset
uspto-grants-2001_09
Patent number
US06288056B1

Reaction notes

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