dimethyl (R)-2-(1-(4-chlorophenyl)-2-nitroethyl)malonate → methyl (3S,4R)-4-(4-chlorophenyl)-2-oxopyrrolidine-3-carboxylate

HRID 2068156Notes

Reaction equation

HRID 2068156 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([CH:13]([C:18]([O:20][CH3:21])=[O:19])[C:14](OC)=[O:15])[CH2:9][N+:10]([O-])=O)=[CH:4][CH:3]=1>[Ni].CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:9][NH:10][C:14](=[O:15])[C@H:13]2[C:18]([O:20][CH3:21])=[O:19])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 11623829dimethyl (R)-2-(1-(4-chlorophenyl)-2-nitroethyl)malonate

Product 1

HCID 40541078methyl (3S,4R)-4-(4-chlorophenyl)-2-oxopyrrolidine-3-carboxylateYield 85.7%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To 210 ml of methanol was added 42.0 g (133 mmol) of dimethyl (R)-2-(1-(4-chlorophenyl)-2-nitroethyl)malonate and developed nickel (21 g), and the mixture was reacted at 35° C. for 8 hours under a hydrogen pressure of 0.5 Mpa (gauge pressure). After completion of the reaction, the nickel catalyst was filtrated, and the filtrate was concentrated under reduced pressure. Ethyl acetate and water were added to cause liquid-separation, the organic layer was concentrate under reduced pressure, and crystallized from heptanes/ethyl acetate. The resultant crystal was filtrated, and dried under reduced pressure, to obtain 28.8 g (114 mmol) of a title compound.

Workup

  1. customthe mixture was reacted at 35° C. for 8 hours under a hydrogen pressure of 0.5 Mpa (gauge pressure)
  2. customAfter completion of the reaction
  3. filtrationthe nickel catalyst was filtrated
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. additionEthyl acetate and water were added
  6. customliquid-separation
  7. concentrationthe organic layer was concentrate under reduced pressure
  8. customcrystallized from heptanes/ethyl acetate
  9. filtrationThe resultant crystal was filtrated
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-edca007f74c741f5b136adb710f49c47
Source dataset
uspto-grants-2012_10
Patent number
US08293926B2

Reaction notes

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