Ethyl 1-methyl-5-oxo-3-phenyl-3-pyrroline-2-carboxylate → (+/-)-(4R*,5R*)-5-(ethoxycarbonyl)-1-methyl-4-phenylpyrrolidin-2-one

HRID 1837980Notes

Reaction equation

HRID 1837980 reaction equation
[CH3:1][N:2]1[C:6](=[O:7])[CH:5]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:3]1[C:14]([O:16][CH2:17][CH3:18])=[O:15]>[Pd].CCO>[CH2:17]([O:16][C:14]([C@@H:3]1[N:2]([CH3:1])[C:6](=[O:7])[CH2:5][C@@H:4]1[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)=[O:15])[CH3:18]

Participants

4

Reactant 1

HCID 11345577Ethyl 1-methyl-5-oxo-3-phenyl-3-pyrroline-2-carboxylate

Product 1

HCID 11379625(+/-)-(4R*,5R*)-5-(ethoxycarbonyl)-1-methyl-4-phenylpyrrolidin-2-oneYield 101.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of ethyl 1-methyl-5-oxo-3-phenyl-3-pyrroline-2-carboxylate (1 g, 4 mmol) and 10% palladium on carbon (0.1 g) in EtOH (30 mL) was stirred under a H2 atmosphere (1 Atm) for 1 hour. The reaction mixture was filtered through a pad of Celite® with the aid of CH2Cl2. The filtrate was concentrated under reduced pressure to yield (±)-(4R*,5R*)-5-(ethoxycarbonyl)-1-methyl-4-phenylpyrrolidin-2-one (1 g, 100%): TLC (40% EtOAc/hex) Rf 0.13; 1H NMR (CDCl3) δ 0.83 (t, J=7.4 Hz, 3H), 2.64-2.72 (dd, J=8.8, 16.5 Hz, 1H), 2.88-3.0 (m, 4H), 3.65-4.0 (m, 4H), 4.34-4.36 (d, J=8.9 Hz, 1H), 7.2-7.35 (m, 5H), HPLC ES-MS m/z (rel abundance) 248 (MH+, 100%).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of Celite® with the aid of CH2Cl2
  2. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f17017e50a704cd48b556ec30208d46f
Source dataset
uspto-grants-2004_08
Patent number
US06784167B2

Reaction notes

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