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

HRID 2257418Notes

Reaction equation

HRID 2257418 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-0de1d4a0b35b46cfaf4d0a11d046fdc0
Source dataset
uspto-grants-1997_08
Patent number
USRE035593

Reaction notes

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