(1RS, 2SR,6RS,7SR)-4-(5-bromo-2-ethylphenyl)-10-oxatricyclo[5.2.1.02,6]-dec-8-en-3,5-dione → (1RS,2SR,6RS,7SR)-4-(5-bromo-2-ethylphenyl)-10-oxatricyclo-[5.2.1.02,6]decane-3,5-dione

HRID 407855Notes

Reaction equation

HRID 407855 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:20][CH3:21])=[C:6]([CH:8]2[C:16](=[O:17])[CH:15]3[CH:10]([CH:11]4[O:18][CH:14]3[CH:13]=[CH:12]4)[C:9]2=[O:19])[CH:7]=1>CO.[Pd]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:20][CH3:21])=[C:6]([CH:8]2[C:9](=[O:19])[CH:10]3[CH:15]([CH:14]4[O:18][CH:11]3[CH2:12][CH2:13]4)[C:16]2=[O:17])[CH:7]=1

Participants

4

Reactant 1

HCID 67284429(1RS, 2SR,6RS,7SR)-4-(5-bromo-2-ethylphenyl)-10-oxatricyclo[5.2.1.02,6]-dec-8-en-3,5-dione

Product 1

HCID 67283919(1RS,2SR,6RS,7SR)-4-(5-bromo-2-ethylphenyl)-10-oxatricyclo-[5.2.1.02,6]decane-3,5-dione

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of (1RS, 2SR,6RS,7SR)-4-(5-bromo-2-ethylphenyl)-10-oxatricyclo[5.2.1.02,6]-dec-8-en-3,5-dione (3.00 g, 8.6 mmol) in methanol (250 ml) is hydrogenated at 3.5 bar over 5% palladium on carbon for 2 hours at room temperature. The catalyst is removed by filtration through diatomaceous earth and the solvent is evaporated under reduced pressure to give (1RS,2SR,6RS,7SR)-4-(5-bromo-2-ethylphenyl)-10-oxatricyclo-[5.2.1.02,6]decane-3,5-dione.

Workup

  1. customThe catalyst is removed by filtration through diatomaceous earth
  2. customthe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-a3959baed8d94041afcddd9cee448262
Source dataset
uspto-grants-2014_06
Patent number
US08754242B2

Reaction notes

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