3-(3-Benzyloxyphenyl)-4-nitrobutyric acid ethyl ester → 4-[3-(Benzyloxy)phenyl]pyrrolidin-2-one

HRID 1819347Notes

Reaction equation

HRID 1819347 reaction equation
C([O:3][C:4](=O)[CH2:5][CH:6]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:12]=1)[CH2:7][N+:8]([O-])=O)C>CCOC(C)=O.CCO.[Ni]>[CH2:18]([O:17][C:13]1[CH:12]=[C:11]([CH:6]2[CH2:7][NH:8][C:4](=[O:3])[CH2:5]2)[CH:16]=[CH:15][CH:14]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 1

HCID 688313563-(3-Benzyloxyphenyl)-4-nitrobutyric acid ethyl ester

Product 1

HCID 688307524-[3-(Benzyloxy)phenyl]pyrrolidin-2-oneYield 75.9%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-(3-benzyloxyphenyl)-4-nitrobutyric acid ethyl ester (3.2 g) in 10 mL EtOAc and 20 mL EtOH was created in a dry round bottom flask. Raney Ni was added and the resulting mixture was stirred under H2 for 10 h at r.t. and filtered through celite. The solution was heated under reflux for 40 h, cooled to r.t., and concentrated. Chromatography of the residue on silica gel (EtOAc:Hexane=1:1 to 3:1) gave 1.89 g of the desired product.

Workup

  1. customwas created in a dry round bottom flask
  2. filtrationfiltered through celite
  3. temperatureThe solution was heated
  4. temperatureunder reflux for 40 h
  5. temperaturecooled to r.t.
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-55d5bec09d47438583784255668369b2
Source dataset
uspto-grants-2009_10
Patent number
US07601742B2

Reaction notes

Loading…