(1S)-N-[2-tert-butoxy-5-(trifluoromethyl)benzyl]-1-isopropyl-4-oxocyclopent-2-ene-1-carboxamide → (1S)-N-[2-tert-butoxy-5-(trifluoromethyl)benzyl]-1-isopropyl-3-oxocyclopentanecarboxamide

HRID 643530Notes

Reaction equation

HRID 643530 reaction equation
[C:1]([O:5][C:6]1[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][C:7]=1[CH2:8][NH:9][C:10]([C@:12]1([CH:18]([CH3:20])[CH3:19])[CH2:16][C:15](=[O:17])[CH:14]=[CH:13]1)=[O:11])([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[Pd]>[C:1]([O:5][C:6]1[CH:24]=[CH:23][C:22]([C:25]([F:26])([F:27])[F:28])=[CH:21][C:7]=1[CH2:8][NH:9][C:10]([C@@:12]1([CH:18]([CH3:20])[CH3:19])[CH2:13][CH2:14][C:15](=[O:17])[CH2:16]1)=[O:11])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 2

HCID 58617127(1S)-N-[2-tert-butoxy-5-(trifluoromethyl)benzyl]-1-isopropyl-4-oxocyclopent-2-ene-1-carboxamideHCID 178418361HCID 178418361, compound

Product 1

HCID 59261028(1S)-N-[2-tert-butoxy-5-(trifluoromethyl)benzyl]-1-isopropyl-3-oxocyclopentanecarboxamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(1S)—N-[2-tert-butoxy-5-(trifluoromethyl)benzyl]-1-isopropyl-4-oxocyclopent-2-ene-1-carboxamide (32 g, 80.6 mmol) was dissolved in MeOH and was hydrogenated for 18 hr with a hydrogen balloon in the presence of a catalytic amount of 10% palladium on carbon. The palladium was filtered through a celite plug. The filtrate was evaporated to dryness to give (1S)—N-[2-tert-butoxy-5-(trifluoromethyl)benzyl]-1-isopropyl-3-oxocyclopentanecarboxamide as a yellow solid.

Workup

  1. filtrationThe palladium was filtered through a celite plug
  2. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-f1a749f8f7d54ea3a689e6438239b402
Source dataset
uspto-grants-2010_04
Patent number
US07700591B2

Reaction notes

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