Bromoacetonitrile → 1-Cyanomethyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester

HRID 2194359Notes

Reaction equation

HRID 2194359 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH2:8][C:7](=[O:10])[NH:6]1)=[O:4].[H-].[Na+].Br[CH2:14][C:15]#[N:16]>CC#N>[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH2:8][C:7](=[O:10])[N:6]1[CH2:14][C:15]#[N:16])=[O:4]

Participants

5

Reactant 3

HCID 11534BromoacetonitrileHCID 24758Sodium hydrideHCID 500249Methyl 5-oxo-DL-prolinate

Product 1

HCID 866498781-Cyanomethyl-5-oxo-pyrrolidine-2-carboxylic acid methyl esterYield 29%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of 5-oxo-pyrrolidine-2-carboxylic acid methyl ester (3 g, 21 mmol) in CH3CN (60 ml), 60% NaH (863 mg, 22 mmol) was added at 0° C. After stirring for 30 minutes, a solution of 2-bromoacetonitrile (2.59 g, 21 mmol) in CH3CN (10 ml) was added dropwise. After warming at room temperature, and stirring for 20 hours, the solvent was evaporated under reduced pressure. The residue was partitioned between water and ethyl acetate, the organic layer was washed with brine, dried (Na2SO4) and evaporated. The residue was purified by flash chromatography (from DCM to DCM/MeOH 95/5 respectively) to afford the title compound as a pale yellow oil (1.1 g, 29% yield).

Workup

  1. stirringstirring for 20 hours
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue was partitioned between water and ethyl acetate
  4. washthe organic layer was washed with brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customThe residue was purified by flash chromatography (from DCM to DCM/MeOH 95/5 respectively)

Sources & evidence

ORD record
ord-7ea53e5afed74e8d89f5c6754c6ac8aa
Source dataset
uspto-grants-2012_12
Patent number
US08334286B2

Reaction notes

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