1-Cyanomethyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester → Tetrahydro-pyrrolo[1,2-a]pyrazine-1,6-dione

HRID 2194360Notes

Reaction equation

HRID 2194360 reaction equation
C[O:2][C:3]([CH:5]1[CH2:9][CH2:8][C:7](=[O:10])[N:6]1[CH2:11][C:12]#[N:13])=O>CO.O=[Pt]=O>[C:3]1(=[O:2])[NH:13][CH2:12][CH2:11][N:6]2[C:7](=[O:10])[CH2:8][CH:9]=[C:5]12

Participants

4

Reactant 1

HCID 866498781-Cyanomethyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester

Product 1

HCID 66867679Tetrahydro-pyrrolo[1,2-a]pyrazine-1,6-dioneYield 63.1%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

1-Cyanomethyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester (1.1 g, 6.04 mmol) was dissolved in MeOH (30 ml) and hydrogenated over PtO2 (200 mg) at 20 psi for 24 hours. After filtration of the catalyst, the solvent was removed under vacuum and the residue triturated with iPrOH to afford the title compound as a white powder (580 mg, 62% yield).

Workup

  1. filtrationAfter filtration of the catalyst
  2. customthe solvent was removed under vacuum
  3. customthe residue triturated with iPrOH

Sources & evidence

ORD record
ord-a6b0968dc79a478b84af28cbee335112
Source dataset
uspto-grants-2012_12
Patent number
US08334286B2

Reaction notes

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