(1R*,5S*)-1-methyl-8-oxabicyclo[3.2.1]oct-6-ene-2,4-dione → (1R*,5S*)-1-methyl-8-oxabicyclo[3.2.1]octane-2,4-dione

HRID 1849971Notes

Reaction equation

HRID 1849971 reaction equation
[CH3:1][C@@:2]12[O:9][C@@H:6]([CH:7]=[CH:8]1)[C:5](=[O:10])[CH2:4][C:3]2=[O:11].[H][H]>C(OCC)(=O)C.[Pd]>[CH3:1][C@@:2]12[O:9][C@@H:6]([CH2:7][CH2:8]1)[C:5](=[O:10])[CH2:4][C:3]2=[O:11]

Participants

5

Reactant 2

HCID 67523953(1R*,5S*)-1-methyl-8-oxabicyclo[3.2.1]oct-6-ene-2,4-dioneHCID 178418361HCID 178418361, compound

Product 1

HCID 67533518(1R*,5S*)-1-methyl-8-oxabicyclo[3.2.1]octane-2,4-dioneYield 56.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (1R*,5S*)-1-methyl-8-oxabicyclo[3.2.1]oct-6-ene-2,4-dione (12.0 g, 0.079 mol) in ethyl acetate (100 ml) is added 10% palladium on carbon (2.4 g), followed by stirring under a 1 bar hydrogen atmosphere for 24 hours. The reaction mixture is then filtered through diatomaceous earth and concentrated to give a crude product which is purified by flash chromatography (hexane/ethyl acetate) to afford (1R*,5S*)-1-methyl-8-oxabicyclo[3.2.1]octane-2,4-dione (6.90 g) as pale yellow solid.

Workup

  1. filtrationThe reaction mixture is then filtered through diatomaceous earth
  2. concentrationconcentrated
  3. customto give a crude product which
  4. customis purified by flash chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-010ce93cba434e06bd9fe9ecd133b3bb
Source dataset
uspto-grants-2015_02
Patent number
US08956999B2

Reaction notes

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