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

HRID 1291238Notes

Reaction equation

HRID 1291238 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[CH:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[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 97.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

In methanol (10 ml) was dissolved ethyl N-tert-butoxycarbonyl-4-piperidylideneacetate (1.20 g) followed by addition of palladium-on-carbon (180 mg). After nitrogen purging, hydrogen gas was introduced and the mixture was stirred at room temperature for 2 hours. The catalyst was then filtered off and the filtrate was concentrated to provide the title compound as white powder (1.18 g). 1H-NMR (CDCl3) δ: 1.1-1.3(2H,m), 1.26(3H,t,J=7.2Hz),1.45(9H,s), 1.6-2.0(3H,m), 2.23(2H,d,J=7.OHz), 2.72(2H,t,J=12.0Hz), 4.0-4.1(2H,m), 4.13(2H,q,J=7.2Hz).

Workup

  1. filtrationThe catalyst was then filtered off
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-1f5bc70d3d934695a39384b80c6335ae
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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