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

HRID 1430762Notes

Reaction equation

HRID 1430762 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:22][CH3:23])=[C:6]([CH:8]2[C:16](=[O:17])[CH:15]3[CH:10]([C:11]4([CH3:20])[O:18][C:14]3([CH3:19])[CH:13]=[CH:12]4)[C:9]2=[O:21])[CH:7]=1>CO.[Pd]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:22][CH3:23])=[C:6]([CH:8]2[C:9](=[O:21])[CH:10]3[CH:15]([C:14]4([CH3:19])[O:18][C:11]3([CH3:20])[CH2:12][CH2:13]4)[C:16]2=[O:17])[CH:7]=1

Participants

4

Reactant 1

HCID 67284135(1RS,2SR,6RS,7SR)-4-(5-bromo-2-ethylphenyl)-1,7-dimethyl-10-oxatricyclo[5.2.1.02,6]dec-8-en-3,5-dione

Product 1

HCID 67283470(1RS,2SR,6RS,7SR)-4-(5-bromo-2-ethylphenyl)-1,7-dimethyl-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)-1,7-dimethyl-10-oxatricyclo[5.2.1.02,6]dec-8-en-3,5-dione (1.63 g, 4.3 mmol) in methanol (200 ml) is hydrogenated at 3.5 bar over 5% palladium on carbon for 1 hour and 30 minutes at room temperature. The catalyst is removed by filtration through diatomaceous earth and the solvent is evaporated under reduced pressure. Trituration with diethyl ether gives (1RS,2SR,6RS,7SR)-4-(5-bromo-2-ethylphenyl)-1,7-dimethyl-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-c67571d702a745c5887115f920378179
Source dataset
uspto-grants-2015_01
Patent number
US08940913B2

Reaction notes

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