Methyl 4-oxo-3-(piperidylmethyl)-4-(3-pyridyl)butanoate → Methyl 3-(3-Pyridylcarbonyl)but-3-enoate

HRID 2184727Notes

Reaction equation

HRID 2184727 reaction equation
[O:1]=[C:2]([C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)[CH:3]([CH2:9]N1CCCCC1)[CH2:4][C:5]([O:7][CH3:8])=[O:6]>C(O)C.Cl.O1CCOCC1>[N:18]1[CH:19]=[CH:20][CH:21]=[C:16]([C:2]([C:3](=[CH2:9])[CH2:4][C:5]([O:7][CH3:8])=[O:6])=[O:1])[CH:17]=1

Participants

4

Reactant 1

HCID 22457748Methyl 4-oxo-3-(piperidylmethyl)-4-(3-pyridyl)butanoate

Product 1

HCID 22457736Methyl 3-(3-Pyridylcarbonyl)but-3-enoateYield 80.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 204431481,4-Dioxane hydrochlorideSolvent

Procedure

A solution of methyl 4-oxo-3-(piperidylmethyl)-4-(3-pyridyl)butanoate (4 g) in ethanol (10 mL) and 4N HCl/dioxane (4.0 mL) was heated at 80° C. for 12 hrs. The reaction mixture was concentrated and purified on flash chromatography (SIO2, CHCl3: MeOH: CH3COOH=10: 1:0.5) to give 2.28 g of the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified on flash chromatography (SIO2, CHCl3: MeOH: CH3COOH=10: 1:0.5)

Sources & evidence

ORD record
ord-746d7d59bc1c4cefb1e9a593c263f6c0
Source dataset
uspto-grants-2002_06
Patent number
US06399606B1

Reaction notes

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