Ethanol → Ethyl 1-azabicyclo[3.3.1]nonane-5-carboxylate

HRID 383937Notes

Reaction equation

HRID 383937 reaction equation
[Br-].C([N+:9]12[CH2:17][C:13]([C:18]([O:20][CH2:21][CH3:22])=[O:19])([CH2:14][CH2:15][CH2:16]1)[CH2:12][CH2:11][CH2:10]2)C1C=CC=CC=1.CCO>[Pd].[C].C(Cl)(Cl)Cl>[N:9]12[CH2:17][C:13]([C:18]([O:20][CH2:21][CH3:22])=[O:19])([CH2:14][CH2:15][CH2:16]1)[CH2:12][CH2:11][CH2:10]2

Participants

5

Reactant 2

HCID 702EthanolHCID 198875961-Benzyl-5-(ethoxycarbonyl)-1-azoniabicyclo[3.3.1]nonane bromide

Product 1

HCID 19887573Ethyl 1-azabicyclo[3.3.1]nonane-5-carboxylateYield 75.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 6212ChloroformSolvent

Procedure

A mixture of 1-benzyl-5-(ethoxycarbonyl)-1-azoniabicyclo[3.3.1]nonane bromide (932 mg), 10% Pd/Carbon with a 50% hydration (25 mg), and EtOH (15 mL) was stirred at room temperature under a hydrogen atmosphere of 3 atm. The reaction mixture was filtered through Celite and the filtrate was concentrated under reduced pressure to obtain a colorless solid. To this solid were added CHCl3 and a saturated aqueous NaHCO3 solution, and the organic layer was separated. Furthermore, the aqueous layer was extracted with CHCl3. The organic layer was collected, dried over MgSO4, and then concentrated under reduced pressure to obtain ethyl 1-azabicyclo[3.3.1]nonane-5-carboxylate (376 mg).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customto obtain a colorless solid
  4. customa saturated aqueous NaHCO3 solution, and the organic layer was separated
  5. extractionFurthermore, the aqueous layer was extracted with CHCl3
  6. customThe organic layer was collected
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4a025ba40c964f5aae9d14f46301d386
Source dataset
uspto-grants-2013_02
Patent number
US08367696B2

Reaction notes

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