HCID 67248823, compound → HCID 67431455, compound

HRID 410482Notes

Reaction equation

HRID 410482 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH3:11])=[O:9])[C:4]([CH:12]([CH3:14])[CH3:13])=[CH:3]1.[H][H]>CO.[Pd]>[O:1]=[C:2]1[CH2:7][CH2:6][C@@H:5]([C:8]([O:10][CH3:11])=[O:9])[C@@H:4]([CH:12]([CH3:14])[CH3:13])[CH2:3]1

Participants

5

Reactant 2

HCID 67248823HCID 67248823, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67431455HCID 67431455, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The product of Step 1 (5.11 g, 26.0 mmol) was dissolved in MeOH (80 ml). Palladium on carbon (0.416 g, 0.391 mmol) was added, and the flask was fitted with a hydrogen balloon. The flask was evacuated and backfilled with hydrogen (3×) and stirred 15 h at room temperature. The reaction was then filtered through Celite and the celite was washed with EtOAc. The filtrate was concentrated in vacuo. Purification via silica gel flash chromatography (0-15% EtOAc:Hexanes) gave methyl(cis)-4-oxo-2-(propan-2-yl)cyclohexanecarboxylate (2.63 g, 51%) as a colorless oil.

Workup

  1. customThe flask was evacuated
  2. filtrationThe reaction was then filtered through Celite
  3. washthe celite was washed with EtOAc
  4. concentrationThe filtrate was concentrated in vacuo
  5. customPurification via silica gel flash chromatography (0-15% EtOAc:Hexanes)

Sources & evidence

ORD record
ord-09af708de1bc44649341f4909873b069
Source dataset
uspto-grants-2014_06
Patent number
US08759366B2

Reaction notes

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