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

HRID 407833Notes

Reaction equation

HRID 407833 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

HCID 2067932010-Oxa-tricyclo[5.2.1.0*2,6*]dec-8-ene-3,5-dione

Product 1

HCID 5935195110-Oxa-tricyclo[5.2.1.0*2,6*]decane-3,5-dione

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

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

  1. customThe catalyst is removed by filtration through diatomaceous earth
  2. 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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