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

HRID 1761176Notes

Reaction equation

HRID 1761176 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-7ce3d032c523426ea8276ef5ef142283
Source dataset
uspto-grants-2005_01
Patent number
US06846835B2

Reaction notes

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