HCID 19738100, compound → HCID 19738113, compound

HRID 2255420Notes

Reaction equation

HRID 2255420 reaction equation
[ClH:1].[CH3:2][CH:3]1[CH:8]2[C:9]([CH:11]([CH3:13])[CH3:12])=[CH:10][CH:5]([CH:6]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:7]2)[N:4]1CC1C=CC=CC=1.[H][H]>[Pd].C(O)C>[ClH:1].[CH3:2][CH:3]1[CH:8]2[C:9]([CH:11]([CH3:12])[CH3:13])=[CH:10][CH:5]([CH:6]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:7]2)[NH:4]1

Participants

5

Reactant 2

HCID 19738100HCID 19738100, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19738113HCID 19738113, compoundYield 100.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of ethyl 3-methyl-8-isopropyl-2-(phenylmethyl)-2-azabicyclo[2.2.2]oct-7-ene-6-carboxylate hydrochloride (23.2 g, 63.8 mmol), ethanol (200 mL) and 10% palladium on carbon (2.3 g) was placed on a Parr hydrogenator at 44 psi of hydrogen pressure for 4 hours. The catalyst was removed by filtration and the solvent was concentrated in vacuo to afford 17.6 g (100%) of ethyl 3-methyl-8-isopropyl-2-azabicyclo[2.2.2]oct-7-ene-6-carboxylate hydrochloride as a white solid.

Workup

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

Sources & evidence

ORD record
ord-d9f22f05994a4c18b6587d1b4612f06f
Source dataset
uspto-grants-1993_08
Patent number
US05240935

Reaction notes

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