Ethyl 3-(nitromethyl)heptanoate → 4-Butylpyrrolidin-2-one
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
Product 1
Reagents, catalysts & solvents 2
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
- customflushed with argon
- filtrationfiltered through a Celite pad
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-374e99d513034b30adb95a0386b6fa3f
- Source dataset
- uspto-grants-2008_11
- Patent number
- US07456211B2
Reaction notes
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