10-Oxa-tricyclo[5.2.1.0*2,6*]dec-8-ene-3,5-dione → 10-Oxa-tricyclo[5.2.1.0*2,6*]decane-3,5-dione
Reaction equation
[CH:1]12[O:10][CH:7]([CH:8]=[CH:9]1)[CH:6]1[CH:2]2[C:3](=[O:12])[CH2:4][C:5]1=[O:11]>CO.[Pd]>[CH:7]12[O:10][CH:1]([CH2:9][CH2:8]1)[CH:2]1[CH:6]2[C:5](=[O:11])[CH2:4][C:3]1=[O:12]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
(1RS,2SR,6RS,7SR)-10-oxatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione (2.1 g, 12.8 mmol), prepared in Step 1, is dissolved in warm methanol (180 ml) and the mixture is allowed to cool to room temperature. The mixture is then hydrogenated in the presence of 5% palladium on carbon (approx. 50 mg) at 3.5 bar for 4 hours. The catalyst is removed by filtration through diatomaceous earth and the filtrate is concentrated under reduced pressure to afford (1RS,2SR,6RS,7SR)-10-oxatricyclo[5.2.1.02,6]decane-3,5-dione.
Workup
- customThe catalyst is removed by filtration through diatomaceous earth
- concentrationthe filtrate is concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-b19fca208a244cc8aad75bf6831d01e5
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08754242B2
Reaction notes
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