HCID 22591691, compound → HCID 22591683, compound

HRID 1784490Notes

Reaction equation

HRID 1784490 reaction equation
[CH3:1][C:2]1([CH2:7]/[CH:8]=[CH:9]/[C:10]23[CH2:17][CH2:16][C:13]([C:18]([O:20][CH3:21])=[O:19])([CH2:14][CH2:15]2)[CH2:12][CH2:11]3)[O:6][CH2:5][CH2:4][O:3]1.[H][H]>C(O)C.[Pd]>[CH3:1][C:2]1([CH2:7][CH2:8][CH2:9][C:10]23[CH2:11][CH2:12][C:13]([C:18]([O:20][CH3:21])=[O:19])([CH2:16][CH2:17]2)[CH2:14][CH2:15]3)[O:3][CH2:4][CH2:5][O:6]1

Participants

5

Reactant 2

HCID 22591691HCID 22591691, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22591683HCID 22591683, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Methyl 4-[(1E)-3-(2-methyl-1,3-dioxolan-2-yl)prop-1-enyl]bicyclo[2.2.2]octane-1-carboxylate (4-B) (1.1 g) was stirred in ethanol (75 mL). A spatula tip scoop of 10% Pd on carbon (150 mg) was added. A hydrogen balloon was added and the mixture was stirred under hydrogen atmosphere for 3 h. The palladium-on-carbon was filtered and the ethanol was removed in vacuo to yield methyl 4-[3-(2-methyl-1,3-dioxolan-2-yl)propyl]bicyclo[2.2.2]octane-1-carboxylate (4-C).

Workup

  1. filtrationThe palladium-on-carbon was filtered
  2. customthe ethanol was removed in vacuo

Sources & evidence

ORD record
ord-bd451761a0974684be9fdb908b83999c
Source dataset
uspto-grants-2009_03
Patent number
US07504402B2

Reaction notes

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