Ethyl 3-(nitromethyl)heptanoate → 4-Butylpyrrolidin-2-one

HRID 273189Notes

Reaction equation

HRID 273189 reaction equation
C([O:3][C:4](=O)[CH2:5][CH:6]([CH2:11][N+:12]([O-])=O)[CH2:7][CH2:8][CH2:9][CH3:10])C.[H][H]>CO.[Ni]>[CH2:7]([CH:6]1[CH2:11][NH:12][C:4](=[O:3])[CH2:5]1)[CH2:8][CH2:9][CH3:10]

Participants

5

Reactant 2

HCID 14463326Ethyl 3-(nitromethyl)heptanoateHCID 178418361HCID 178418361, compound

Product 1

HCID 141781014-Butylpyrrolidin-2-oneYield 91%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a solution of 3-nitromethylheptanoic acid ethyl ester (10 g, 49.2 mmol) in methanol (100 mL) under argon was added Raney Ni (5 g). The mixture was stirred under 50 psi of hydrogen for 48 h, flushed with argon, filtered through a Celite pad, and concentrated under vacuum to afford 4-butylpyrrolidin-2-one as a colorless oil (6.3 g, 91%). MS(ES) m/e 142 [M+H]+.

Workup

  1. customflushed with argon
  2. filtrationfiltered through a Celite pad
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-374e99d513034b30adb95a0386b6fa3f
Source dataset
uspto-grants-2008_11
Patent number
US07456211B2

Reaction notes

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