HCID 58481436, compound → HCID 58481474, compound

HRID 509174Notes

Reaction equation

HRID 509174 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11](/[CH:14]=[C:15]2/[C:16](=[O:31])[C:17]([C:22]3[C:27]([CH3:28])=[CH:26][C:25]([CH3:29])=[CH:24][C:23]=3[CH3:30])=[C:18]([O:20][CH3:21])[CH2:19]/2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([CH2:14][CH:15]2[CH2:19][C:18]([O:20][CH3:21])=[C:17]([C:22]3[C:27]([CH3:28])=[CH:26][C:25]([CH3:29])=[CH:24][C:23]=3[CH3:30])[C:16]2=[O:31])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 58481436HCID 58481436, compound

Product 1

HCID 58481474HCID 58481474, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 4-[4-methoxy-2-oxo-3-(2,4,6-trimethyl-phenyl)-cyclopent-3-en-(E)-ylidenemethyl]-piperidine-1-carboxylic acid tert-butyl ester (15.33 g, 36.02 mmol) in ethanol (150 ml) is added 10% palladium on activated charcoal (1.53 g) and the reaction stirred under hydrogen (4 bar) for hours. The reaction is filtered through a pad of Celite and the solvent removed under reduced pressure to give 4-[4-methoxy-2-oxo-3-(2,4,6-trimethyl-phenyl)-cyclopent-3-enylmethyl]-piperidine-1-carboxylic acid tert-butyl ester (15.4 g)

Workup

  1. filtrationThe reaction is filtered through a pad of Celite
  2. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-be98c1c6402e4eeca8227ef645985158
Source dataset
uspto-grants-2015_08
Patent number
US09096560B2

Reaction notes

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