HCID 67248823, compound → HCID 67431455, compound

HRID 1039973Notes

Reaction equation

HRID 1039973 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-5eb88e9e9e5846459edc691583d74b8a
Source dataset
uspto-grants-2013_10
Patent number
US08551984B2

Reaction notes

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