HCID 45088408, compound → HCID 12648939, compound

HRID 497080Notes

Reaction equation

HRID 497080 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 45088408HCID 45088408, compound

Product 1

HCID 12648939HCID 12648939, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

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

  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-0ac0d5d068e34cf2a7fa6d5e9dc9d04b
Source dataset
uspto-grants-2005_09
Patent number
US06949553B2

Reaction notes

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