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

HRID 1587369Notes

Reaction equation

HRID 1587369 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 hydrobromideYield 84.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of ethyl 1-benzyl-1-azoniabicyclo[2.2.1]hept-4-ylcarboxylate bromide (D12, 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 (D13) 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-680b660fb8294e60b9b8ce26a488b508
Source dataset
uspto-grants-1993_06
Patent number
US05217975

Reaction notes

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