1,1-Dimethylethyl 4-(3-ethoxy-3-oxo-1-propen-1-yl)-1-piperidinecarboxylate → tert-Butyl 4-(3-ethoxy-3-oxopropyl)piperidine-1-carboxylate

HRID 458755Notes

Reaction equation

HRID 458755 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH:5]=[CH:6][CH:7]1[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]1)[CH3:2].[H][H]>C(O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:20])[CH2:5][CH2:6][CH:7]1[CH2:8][CH2:9][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:11][CH2:12]1)[CH3:2]

Participants

5

Reactant 2

HCID 533949841,1-Dimethylethyl 4-(3-ethoxy-3-oxo-1-propen-1-yl)-1-piperidinecarboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 23245138tert-Butyl 4-(3-ethoxy-3-oxopropyl)piperidine-1-carboxylateYield 69.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 1.0 g of t-butyl 4-(3-ethoxy-3-oxoprop-1-enyl)-tetrahydropyridine-1(2H)-carboxylate (cf. WO9501336) in 20 ml of ethanol, 300 mg of 10% palladium-on-carbon catalyst, and stirred for 3 hours in a hydrogen atmosphere, at ambient temperature and pressure. After filtering the catalyst off, the solvent was distilled off under reduced pressure to provide 700 mg of the title compound.

Workup

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

Sources & evidence

ORD record
ord-3c5b2af50d8f4e0fafb717b8732e105a
Source dataset
uspto-grants-2007_03
Patent number
US07192969B2

Reaction notes

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