HCID 54389077, compound → HCID 53754019, compound

HRID 1752289Notes

Reaction equation

HRID 1752289 reaction equation
[C:1]([C:3]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:4][C:5](OCC)=[O:6])#[N:2]>CCO.[Ni]>[O:6]=[C:5]1[NH:2][CH2:1][C:3]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:4]1

Participants

4

Reactant 1

HCID 54389077HCID 54389077, compound

Product 1

HCID 53754019HCID 53754019, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A mixture of diethyl 3-cyano-3-phenylpentanedioate (8 g, 27.7 mmol) and Raney-Ni (4 g) in EtOH (240 mL) was stirred under H2 atmosphere (50 psi) at rt for 2 days. TLC and LC-MS showed that the reaction was completed, the reaction mixture was filtered through Celite, and the filtrate was concentrated under reduced pressure to dryness. The residue was purified by chromatography on a silica gel column eluting with PE/EtOAc=10:11:8 to give ethyl 2-(5-oxo-3-phenylpyrrolidin-3-yl)acetate (4.8 g, yield 71%) as white solid. 1H NMR (CDCl3 400 MHz): δ 7.33 (t, 2H), 7.24 (t, 1H), 7.18 (d, 2H), 5.79 (s, 1H), 3.97-3.88 (m, 3H), 3.72 (d, 1H), 2.86-2.70 (m, 4H), 1.03 (t, 3H).

Workup

  1. filtrationthe reaction mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated under reduced pressure to dryness
  3. customThe residue was purified by chromatography on a silica gel column
  4. washeluting with PE/EtOAc=10:11:8

Sources & evidence

ORD record
ord-719d1b64f6df4072ab6091831bb1ea06
Source dataset
uspto-grants-2015_10
Patent number
US09163012B2

Reaction notes

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