HCID 12880279, compound → HCID 19738105, compound

HRID 2255416Notes

Reaction equation

HRID 2255416 reaction equation
[ClH:1].[C:2]1([CH2:8][CH:9]2[CH:14]3[C:15]([CH2:17][CH3:18])=[CH:16][CH:11]([CH:12]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:13]3)[N:10]2[CH3:24])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Pd].C(O)C>[ClH:1].[C:2]1([CH2:8][CH:9]2[CH:14]3[CH:15]([CH2:17][CH3:18])[CH2:16][CH:11]([CH:12]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:13]3)[N:10]2[CH3:24])[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 12880279HCID 12880279, compound

Product 1

HCID 19738105HCID 19738105, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of ethyl 3-(phenylmethyl)-8-ethyl-2-methyl-2-azabicyclo[2.2.2]oct-7-ene-6-carboxylate hydrochloride (23.2 g, 0.067 mol), ethanol (300 mL) and 10% palladium on carbon (1.0 g) was placed on a Parr hydrogenator at approximately 50 psi and was heated to 50° C. for 3 hours and 20 minutes. The catalyst was removed by filtration and the filtrate was concentrated in vacuo. The residue was dissolved in hot ethanol and cooled on an ice-bath. The precipitate which formed was collected by filtration and dried at 40° C. in vacuo to afford 17.2 g (73%) of ethyl 3-(phenylmethyl)-8-ethyl-2-methyl-2-azabicyclo[2.2.2]octane-6-carboxylate hydrochloride, m.p. 226°-227° C.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. dissolutionThe residue was dissolved in hot ethanol
  4. temperaturecooled on an ice-bath
  5. customThe precipitate which formed
  6. filtrationwas collected by filtration
  7. customdried at 40° C. in vacuo

Sources & evidence

ORD record
ord-5d61661c328e4e07a3e415c548f8670d
Source dataset
uspto-grants-1993_08
Patent number
US05240935

Reaction notes

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