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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 1761178
Notes
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Reaction equation

HRID 1761178 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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-39448a4134e942fc9fe900b5c2c13bcf
Source dataset
uspto-grants-2005_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06846835B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes