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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 1785270
Notes
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Reaction equation

HRID 1785270 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-a295b1c4a76243d89cb4d499c6467ed8
Source dataset
uspto-grants-2009_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07504432B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes