HCID 45088409, compound → [(2S)-1-Methylpyrrolidin-2-yl]acetonitrile

HRID 497074Notes

Reaction equation

HRID 497074 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

HCID 45088409HCID 45088409, compound

Product 1

HCID 12648940[(2S)-1-Methylpyrrolidin-2-yl]acetonitrile

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

Raney-Ni (1.5 ml) was added to an EtOH (30 ml) solution of the 2-((2S)-1-methyl-5-thioxopyrrolidin-2-yl)ethanenitrile (940 mg, 6.1 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-((2S)-1-methylpyrrolidin-2-yl)ethanenitrile as a mixture (195 mg) with impurities difficult to separate.

Workup

  1. temperaturethe mixture was heated for 24 hours
  2. temperatureunder reflux (upon TCL
  3. filtrationThe inorganic matter was filtered off
  4. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-5d80ff94621648ffb2825c37a91dc7d3
Source dataset
uspto-grants-2005_09
Patent number
US06949553B2

Reaction notes

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