3-(Pyridin-3-yl)cyclohex-2-en-1-one → 3-(Pyridin-3-yl)cyclohexanone

HRID 571965Notes

Reaction equation

HRID 571965 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH2:12][CH2:11][CH2:10][C:9](=[O:13])[CH:8]=2)[CH:2]=1>CCO.[Rh]>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]2[CH2:12][CH2:11][CH2:10][C:9](=[O:13])[CH2:8]2)[CH:2]=1

Participants

4

Reactant 1

HCID 134025713-(Pyridin-3-yl)cyclohex-2-en-1-one

Product 1

HCID 221008783-(Pyridin-3-yl)cyclohexanone

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 8b (275 mg, 1.59 mmol) and rhodium (325 mg, 0.158 mmol, 5% wt. on activated basic alumina) in EtOH (16.0 mL) was hydrogenated at atmospheric pressure while stirring at rt. After the reaction was deemed to be complete, the reaction mixture was filtered through a short column of Celite®, eluting copiously with EtOAc, and the combined organics were concentrated in vacuo to afford the title compound, 8c. m/z (ES) 176 (MH)+

Workup

  1. filtrationthe reaction mixture was filtered through a short column of Celite®
  2. washeluting copiously with EtOAc
  3. concentrationthe combined organics were concentrated in vacuo

Sources & evidence

ORD record
ord-283f7020abbc4d20938ad049ade03a67
Source dataset
uspto-grants-2015_05
Patent number
US09029377B2

Reaction notes

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