HCID 19097417, compound → HCID 19097409, compound

HRID 1975317Notes

Reaction equation

HRID 1975317 reaction equation
[ClH:1].[CH3:2][CH:3]1[C:8]2([CH3:12])[C:9]([CH3:11])=[CH:10][CH:5]([CH:6]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:7]2)[N:4]1CC1C=CC=CC=1>[Pd].C(O)C>[ClH:1].[CH3:2][CH:3]1[C:8]2([CH3:12])[CH:9]([CH3:11])[CH2:10][CH:5]([CH:6]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:7]2)[NH:4]1

Participants

4

Reactant 1

HCID 19097417HCID 19097417, compound

Product 1

HCID 19097409HCID 19097409, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of ethyl 3,4,8-trimethyl-2-(phenylmethyl)-2-azabicyclo[2.2.2]oct-7-ene-6-carboxylate hydrochloride (26.2 g, mmol), 10% palladium on carbon (2.6 g) and ethanol (200 mL) were placed on a Parr hydrogenator at 50 psi for 3.5 hours. The catalyst was removed by filtration and the solvent was removed in vacuo to afford crude ethyl 3,4,8-trimethyl-2-azabicyclo[2.2.2]octane-6-carboxylate hydrochloride as a yellow oil, which was used directly in the next step.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-c9908c525098462aba3e4cafee7f9020
Source dataset
uspto-grants-1994_02
Patent number
US05286733

Reaction notes

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