Ethyl 4-(N-BOC-4-piperidyl)trans-crotonate → Tert-butyl 4-(4-ethoxy-4-oxobutyl)piperidine-1-carboxylate

HRID 636677Notes

Reaction equation

HRID 636677 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14]/[CH:15]=[CH:16]/[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]>CCOC(C)=O.[Pd]>[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

4

Reactant 1

HCID 10017534Ethyl 4-(N-BOC-4-piperidyl)trans-crotonate

Product 1

HCID 10334920Tert-butyl 4-(4-ethoxy-4-oxobutyl)piperidine-1-carboxylateYield 92.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The olefin of Example 5 (2.6 g, 8.7 mmol) in EtOAc (50 mL) at room temperature is stirred under a hydrogen atmosphere (1 atm) in the presence of 10% Pd/C (500 mg) overnight. The reaction mixture is then purged with argon, followed by filtration through a Celite pad. Concentration of the filtrate followed by flash chromatography (10% EtOAc in hexane) gave the title ester (2.4 g, 92%) as a crystalline solid.

Workup

  1. customThe reaction mixture is then purged with argon
  2. filtrationfollowed by filtration through a Celite pad

Sources & evidence

ORD record
ord-885c7ab98ab240a69e9c6b79ff7aba8e
Source dataset
uspto-grants-2001_02
Patent number
US06194435B1

Reaction notes

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