tert-Butyl 4-(2-ethoxy-2-oxoethylidene)piperidine-1-carboxylate → Ethyl 1-((1,1-dimethylethoxy)carbonyl)-4-piperidineacetate

HRID 1785268Notes

Reaction equation

HRID 1785268 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[CH:5]=[C:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1)[CH3:2].[H][H]>CO.[Pd]>[CH2:1]([O:3][C:4](=[O:19])[CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1)[CH3:2]

Participants

5

Reactant 2

HCID 10333298tert-Butyl 4-(2-ethoxy-2-oxoethylidene)piperidine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 9993342Ethyl 1-((1,1-dimethylethoxy)carbonyl)-4-piperidineacetateYield 93.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 355 mg of t-butyl 4-(2-ethoxy-2-oxoethylidene)tetrahydropyridine-1(2H)-carboxylate in 10 ml of methanol, 50 mg of 10% palladium-on-carbon catalyst was added and stirred for 13 hours in 3 atmospheres' hydrogen pressure. Filtering the catalyst off, the solvent was distilled off under reduced pressure to provide 334 mg of the title compound.

Workup

  1. filtrationFiltering the catalyst off, the solvent
  2. distillationwas distilled off under reduced pressure

Sources & evidence

ORD record
ord-261116ed74f64cfb8097dccb58c8d003
Source dataset
uspto-grants-2009_03
Patent number
US07504432B2

Reaction notes

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