HCID 45088408, compound → HCID 12648939, compound
Reaction equation
[CH3:1][N:2]1[C:6](=S)[CH2:5][CH2:4][C@@H:3]1[CH2:8][C:9]#[N:10]>[Ni].CCO>[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][C@@H:3]1[CH2:8][C:9]#[N:10]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
Raney-Ni (1.5 ml) was added to an EtOH (30 ml) solution of the 2-((2R)-1-methyl-5-thioxopyrrolidin-2-yl)ethanenitrile (1.36 g, 8.8 mmols), and the mixture was heated for 24 hours under reflux (Upon TCL, the starting materials had not completely disappeared). The inorganic matter was filtered off, and then the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography (SiO2 40 g, MeOH—CHCl3 1:9 v/v) to obtain 2-((2R)-1-methylpyrrolidin-2-yl)ethanenitrile as a mixture (498 mg) with impurities difficult to separate.
Workup
- temperaturethe mixture was heated for 24 hours
- temperatureunder reflux (Upon TCL
- filtrationThe inorganic matter was filtered off
- distillationthe solvent was distilled off under reduced pressure
Sources & evidence
- ORD record
- ord-0ac0d5d068e34cf2a7fa6d5e9dc9d04b
- Source dataset
- uspto-grants-2005_09
- Patent number
- US06949553B2
Reaction notes
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