Methanol → Methyl [2-oxo-1-(2-phenylethyl)pyrrolidin-3-yl]acetate

HRID 2240579Notes

Reaction equation

HRID 2240579 reaction equation
[CH3:1][O:2][C:3](=[O:18])[CH2:4][C:5]1[C:6](=[O:17])[N:7]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:8][CH:9]=1.[H][H].[CH3:21]O>[Pd]>[CH3:1][O:2][C:3](=[O:18])[CH2:4][CH:5]1[CH2:9][CH2:8][N:7]([CH2:10][CH2:11][C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:21]=2)[C:6]1=[O:17]

Participants

5

Reactant 3

HCID 887MethanolHCID 57443415(1-benzyl-2-oxo-2,5-dihydro-1H-pyrrol-3-yl)-acetic acid methyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 21750807Methyl [2-oxo-1-(2-phenylethyl)pyrrolidin-3-yl]acetateYield 95%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

30 mg of (1-benzyl-2-oxo-2,5-dihydro-1H-pyrrol-3-yl)-acetic acid methyl ester was dissolved in methanol solution (0.12 mM) under nitrogen atmosphere. Then 2.6 mg of Pd—C (0.02 mM) was added thereto, and hydrogenated under a hydrogen balloon for 1 to 2 hrs at room temperature. The reaction mixture was filtered and concentrated in vacuo. The resulting compound was purified with Silica gel column chromatography with a solvent mixture mixed with EtOAc and hexane (1:1) as an eluant to give (2-oxo-1-phenethyl-pyrrolidin-3-yl)-acetic acid methyl ester (25r) (yield: 95%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated in vacuo
  3. customThe resulting compound was purified with Silica gel column chromatography with a solvent mixture
  4. additionmixed with EtOAc and hexane (1:1) as an eluant

Sources & evidence

ORD record
ord-7d60a20f321a4d69ba3cd6ca3117b0a8
Source dataset
uspto-grants-2010_05
Patent number
US07723376B2

Reaction notes

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