HCID 86705477, compound → HCID 68294966, compound

HRID 2279460Notes

Reaction equation

HRID 2279460 reaction equation
C([C@H]1COC(=O)N1[C:14](=[O:29])[CH2:15][C@@H:16]([C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([F:28])[CH:22]=1)[CH2:17][N+:18]([O-])=O)C1C=CC=CC=1>CCOC(C)=O.CCO.[Ni]>[Cl:27][C:24]1[CH:25]=[CH:26][C:21]([C@H:16]2[CH2:17][NH:18][C:14](=[O:29])[CH2:15]2)=[CH:22][C:23]=1[F:28]

Participants

4

Reactant 1

HCID 86705477HCID 86705477, compound

Product 1

HCID 68294966HCID 68294966, compoundYield 50.9%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

To a solution of 88 (1.55 g, 3.68 mmol) in EtOAc/EtOH (1:1, 50 mL) was added a Raney Nickel suspension (0.316 g, 3.68 mmol) and the reaction mixture was purged with nitrogen then placed under 40 psi hydrogen for 20 h. A second aliquot of Raney Ni suspension (1 mL) was added and the reaction was placed under hydrogen pressure for another 24 h. A third aliquot of Raney Ni was added (1 mL) and the reaction was placed under hydrogen pressure of 45 psi for 24 h. The reaction was filtered through a plug of CELITE® and the filtrate was concentrated. The crude product was purified by SiO2 chromatography eluting with an EtOAc/hexane gradient (10 to 30% EtOAc) to afford 400 mg (50.8%) of (S)-4-(4-chloro-3-fluorophenyl)pyrrolidin-2-one (90).

Workup

  1. customthe reaction mixture was purged with nitrogen
  2. additionA second aliquot of Raney Ni suspension (1 mL) was added
  3. customfor another 24 h
  4. additionA third aliquot of Raney Ni was added (1 mL)
  5. customfor 24 h
  6. filtrationThe reaction was filtered through a plug of CELITE®
  7. concentrationthe filtrate was concentrated
  8. customThe crude product was purified by SiO2 chromatography
  9. washeluting with an EtOAc/hexane gradient (10 to 30% EtOAc)

Sources & evidence

ORD record
ord-f2fab6b725984f51a277e64a0f61c0d7
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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