HCID 10487712, compound → HCID 12886283, compound

HRID 231068Notes

Reaction equation

HRID 231068 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6]([CH3:13])([CH3:12])[NH:7][C:8]([CH3:11])([CH3:10])[CH:9]=1)=[O:4]>CO.[Ni]>[CH3:1][O:2][C:3]([CH:5]1[CH2:9][C:8]([CH3:11])([CH3:10])[NH:7][C:6]1([CH3:13])[CH3:12])=[O:4]

Participants

4

Reactant 1

HCID 10487712HCID 10487712, compound

Product 1

HCID 12886283HCID 12886283, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

87.80 g (479 mmol) of 2,2,5,5-tetramethyl-3-pyrroline-3-carboxylic acid methyl ester is dissolved in 1,000 ml of methanol and hydrogenated in the presence of 11 g of Raney nickel at room temperature under an initial pressure of 180 bar. The mixture is removed from the catalyst by suctioning, the solution is treated with activated carbon, concentrated under vacuum, and the residue is distilled with the aid of a water-jet aspirator. The methyl ester of 2,2,5,5-tetramethylpyrrolidine-3-carboxylic acid passes over at 86°-87°/14 mm. Yield: 77.1 g (88% of theory). As per analysis by gas chromatography, the compound has a purity of 98.7%.

Workup

  1. customThe mixture is removed from the catalyst
  2. additionthe solution is treated with activated carbon
  3. concentrationconcentrated under vacuum
  4. distillationthe residue is distilled with the aid of a water-jet aspirator
  5. custompasses over at 86°-87°/14 mm

Sources & evidence

ORD record
ord-3f3043509f60481ca520b56b79dc8dfa
Source dataset
uspto-grants-1989_07
Patent number
US04845090

Reaction notes

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