1-Benzyl-4-(ethoxycarbonyl)-1-azoniabicyclo[2.2.1]heptane bromide → Ethyl 1-azabicyclo[2.2.1]heptane-4-carboxylate hydrobromide

HRID 1197826Notes

Reaction equation

HRID 1197826 reaction equation
[Br-:1].C([N+:9]12[CH2:15][C:12]([C:16]([O:18][CH2:19][CH3:20])=[O:17])([CH2:13][CH2:14]1)[CH2:11][CH2:10]2)C1C=CC=CC=1>C(O)C.[Pd]>[BrH:1].[N:9]12[CH2:15][C:12]([C:16]([O:18][CH2:19][CH3:20])=[O:17])([CH2:11][CH2:10]1)[CH2:13][CH2:14]2

Participants

4

Reactant 1

HCID 229227801-Benzyl-4-(ethoxycarbonyl)-1-azoniabicyclo[2.2.1]heptane bromide

Product 1

HCID 22922786Ethyl 1-azabicyclo[2.2.1]heptane-4-carboxylate hydrobromide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of ethyl 1-benzyl-1-azoniabicyclo[2.2.1]hept-4-ylcarboxylate bromide (D16, 130 g, 0.38 mole) in ethanol (500 ml) was hydrogenated over 10% palladium on charcoal catalyst (8 g) at atmospheric temperature and pressure for 18 h. The catalyst was removed by filtering through celite, washing several times with hot ethanol, and the filtrate concentrated in vacuo to give the title compound (D17) as a crystalline white solid (80.1 g, 84%).

Workup

  1. customThe catalyst was removed
  2. filtrationby filtering through celite
  3. washwashing several times with hot ethanol
  4. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-3c65bb1b631543f0a4b135cdf59784ec
Source dataset
uspto-grants-1994_01
Patent number
US05278170

Reaction notes

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