Methyl 6-(bicyclo[2.2.2]oct-5-ene-2-ylsulphonylmethyl)-3-(furan-3-yl)-2-methoxybenzoate → Methyl 6-(bicyclo[2.2.2]octane-2-ylsulphonylmethyl)-3-(furan-3-yl)-2-methoxybenzoate

HRID 2177821Notes

Reaction equation

HRID 2177821 reaction equation
[CH:1]12[CH2:8][CH2:7][CH:4]([CH:5]=[CH:6]1)[CH2:3][CH:2]2[S:9]([CH2:12][C:13]1[C:18]([C:19]([O:21][CH3:22])=[O:20])=[C:17]([O:23][CH3:24])[C:16]([C:25]2[CH:29]=[CH:28][O:27][CH:26]=2)=[CH:15][CH:14]=1)(=[O:11])=[O:10].[H][H]>[Pd].C1COCC1.C(O)C>[CH:1]12[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8]1)[CH2:3][CH:2]2[S:9]([CH2:12][C:13]1[C:18]([C:19]([O:21][CH3:22])=[O:20])=[C:17]([O:23][CH3:24])[C:16]([C:25]2[CH:29]=[CH:28][O:27][CH:26]=2)=[CH:15][CH:14]=1)(=[O:11])=[O:10]

Participants

6

Reactant 2

HCID 67107910Methyl 6-(bicyclo[2.2.2]oct-5-ene-2-ylsulphonylmethyl)-3-(furan-3-yl)-2-methoxybenzoate2×HCID 178418361HCID 178418361, compound

Product 1

HCID 67107595Methyl 6-(bicyclo[2.2.2]octane-2-ylsulphonylmethyl)-3-(furan-3-yl)-2-methoxybenzoateYield 11.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 6-(bicyclo[2.2.2]oct-5-ene-2-ylsulphonylmethyl)-3-(furan-3-yl)-2-methoxybenzoate (Intermediate 170, 0.26 g) and palladium on carbon (10%, 0.01 g) in THF (15 ml) and ethanol (10 ml) was stirred in an atmosphere of hydrogen (balloon) for 1 hour. The mixture was filtered through Celite and the filtrate was evaporated to dryness. The residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate in cyclohexane with a gradient of 10-50% to give methyl 6-(bicyclo[2.2.2]octane-2-ylsulphonylmethyl)-3-(furan-3-yl)-2-methoxybenzoate (0.029 g).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. customthe filtrate was evaporated to dryness
  3. customThe residue was purified by chromatography on silica
  4. washeluting with a mixture of ethyl acetate in cyclohexane with a gradient of 10-50%

Sources & evidence

ORD record
ord-1e3ef6869c9849a982c49904e66a0266
Source dataset
uspto-grants-2015_06
Patent number
US09067905B2

Reaction notes

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