HCID 66867027, compound → HCID 68089186, compound

HRID 1631895Notes

Reaction equation

HRID 1631895 reaction equation
[CH:1]1([CH:4]=[C:5]2[CH2:9][C:8](=[O:10])[CH:7]([C:11]3[C:16]([CH3:17])=[CH:15][C:14]([CH3:18])=[CH:13][C:12]=3[CH3:19])[C:6]2=[O:20])[CH2:3][CH2:2]1>CO.[Pd]>[CH:1]1([CH2:4][CH:5]2[CH2:9][C:8](=[O:10])[CH:7]([C:11]3[C:16]([CH3:17])=[CH:15][C:14]([CH3:18])=[CH:13][C:12]=3[CH3:19])[C:6]2=[O:20])[CH2:2][CH2:3]1

Participants

4

Reactant 1

HCID 66867027HCID 66867027, compound

Product 1

HCID 68089186HCID 68089186, compoundYield 20.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To 5% w/w Pd/C (5 mg) was added a solution of 4-[1-cyclopropyl-methylidene]-2-(2,4,6-trimethyl-phenyl)-cyclopentane-1,3-dione (28 mg, 0.09 mmol) in MeOH (10 ml). The reaction was stirred under an atmosphere of H2 (1.5 bar) for 1.5 hours, filtered through a pad of celite and washed through with MeOH (20 ml). The solvent was removed under reduced pressure to give the crude product (20 mg) which was purified by mass-directed HPLC to give the desired product (5 mg).

Workup

  1. filtrationfiltered through a pad of celite
  2. washwashed through with MeOH (20 ml)
  3. customThe solvent was removed under reduced pressure
  4. customto give the crude product (20 mg) which
  5. customwas purified by mass-directed HPLC

Sources & evidence

ORD record
ord-2094668dcb41490aa1c7658823e07279
Source dataset
uspto-grants-2014_07
Patent number
US08791303B2

Reaction notes

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