HCID 69891907, compound → HCID 69891891, compound

HRID 1837968Notes

Reaction equation

HRID 1837968 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]([N:11]2[C:15](=[O:16])[CH:14]=[C:13]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:12]2[C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH3:10])=[CH:5][CH:4]=1>[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C@@H:9]([N:11]2[C:15](=[O:16])[CH2:14][C@H:13]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[C@@H:12]2[C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH3:10])=[CH:7][CH:8]=1

Participants

3

Reactant 1

HCID 69891907HCID 69891907, compound

Product 1

HCID 69891891HCID 69891891, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of ethyl 1-[(1S)-1-(4-methoxyphenyl)ethyl]-5-oxo-3-phenyl-3-pyrroline-2-carboxylate (5 g, 13.7 mmol) and 10% palladium on carbon (0.5 g) was maintained under a H2 atmosphere (55 psi) overnight. The resulting mixture was filtered through a plug of Celite© and silica gel to give ethyl cis-1-[(1S)-1-(4-methoxyphenyl)ethyl]-5-oxo-3-phenylpyrrolidine-2-carboxylate (5 g, 100%). The mixture of diastereomers was triturated (Et2O) to give (4R,5R)-5-(ethoxycarbonyl)-1-(4-methoxyphenyl)ethyl]-4-phenylpyrrolidin-2-one (2.0 g, 40%): 1H NMR (CDCl3) δ 0.62 (t, J=7.1 Hz, 3H). 1.60 (d, J=6.9 Hz, 3H), 2.60 (q, J=8.1 Hz, 1H), 3.09-3.30 (m, 3H), 3.70-3.88 (m, 4H), 4.31 (d, J=8.3 Hz, 1H), 5.52 (q, J=7.3 Hz, 1H), 6.76-6.82 (m, 2H), 7.15-7.31 (m, 7H); HPLC ES-MS m/z (rel abundance) 368 (MH+, 100%).

Workup

  1. temperaturewas maintained under a H2 atmosphere (55 psi) overnight
  2. filtrationThe resulting mixture was filtered through a plug of Celite© and silica gel

Sources & evidence

ORD record
ord-3990b16f82554d9682f709ebc09284a6
Source dataset
uspto-grants-2004_08
Patent number
US06784167B2

Reaction notes

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