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

HRID 407846Notes

Reaction equation

HRID 407846 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[CH:10]1[C:18](=[O:19])[CH:17]2[CH:12]([CH:13]3[O:20][CH:16]2[CH:15]=[CH:14]3)[C:11]1=[O:21]>CO.[Pd]>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[CH:10]1[C:11](=[O:21])[CH:12]2[CH:17]([CH:16]3[O:20][CH:13]2[CH2:14][CH2:15]3)[C:18]1=[O:19]

Participants

4

Reactant 1

HCID 67283862(1RS,2SR,6RS,7SR)-4-(2,4,6-trimethylphenyl)-10-oxatricyclo-[5.2.1.02,6]dec-8-en-3,5-dione

Product 1

HCID 67284407(1RS,2SR,6RS,7SR)-4-(2,4,6-trimethylphenyl)-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-(2,4,6-trimethylphenyl)-10-oxatricyclo[5.2.1.02,6]dec-8-en-3,5-dione (205 mg, 0.66 mmol) in methanol (250 ml) is hydrogenated at 2 bar over 5% palladium on carbon (approximately 20 mgs) for 1 hour 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-(2,4,6-trimethylphenyl)-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-eb788b9f3513458f9979a94c24b56ae4
Source dataset
uspto-grants-2014_06
Patent number
US08754242B2

Reaction notes

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