3-Pyridineacrylic acid ethyl ester → Ethyl 3-(piperidin-3-yl)propanoate

HRID 1066783

Reaction equation

HRID 1066783 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=[CH:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:2]=1>C(O)C.[Rh]>[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([CH2:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:2]1

Participants

4

Reactant 1

HCID 5833373-Pyridineacrylic acid ethyl ester

Product 1

HCID 21186558Ethyl 3-(piperidin-3-yl)propanoateYield 63%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 702EthanolSolvent

Procedure

A solution of ethyl 3-[pyrid-3-yl]prop-2-enoate (60 g, 0.34 mol) in ethanol (600 ml) was treated with 5% rhodium on alumina powder (17.2 g). The mixture was placed under a hydrogen atmosphere (55 psi) for five hours at 60° C. The reaction was stopped by removing the hydrogen and the reaciton mixture was filtered through a layer of CELITE™. The residue was washed with hot ethanol. The filtrate was concentrated and purified by flash chromatography to provide 39.6 grams (63%) of the desired title product. IR, NMR, and IR were consistent with the proposed title structure.

Workup

  1. customfor five hours
  2. customat 60° C
  3. customby removing the hydrogen
  4. filtrationthe reaciton mixture was filtered through a layer of CELITE™
  5. washThe residue was washed with hot ethanol
  6. concentrationThe filtrate was concentrated
  7. custompurified by flash chromatography

Sources & evidence

ORD record
ord-4e6e8b93b9cb4da98df567de9fdceaac
Source dataset
uspto-grants-2001_06
Patent number
US06245761B1

Linked notes

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