Hydrochloric Acid → 1-Azabicyclo[3.3.1]nonane-5-carboxylic acid hydrochloride

HRID 654520Notes

Reaction equation

HRID 654520 reaction equation
[Br-].C([N+:9]12[CH2:17][C:13]([C:18]([O:20]CC)=[O:19])([CH2:14][CH2:15][CH2:16]1)[CH2:12][CH2:11][CH2:10]2)C1C=CC=CC=1.[H][H].[ClH:25]>C(O)C.[Pd]>[ClH:25].[N:9]12[CH2:17][C:13]([C:18]([OH:20])=[O:19])([CH2:14][CH2:15][CH2:16]1)[CH2:12][CH2:11][CH2:10]2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 198875961-Benzyl-5-(ethoxycarbonyl)-1-azoniabicyclo[3.3.1]nonane bromideHCID 178418361HCID 178418361, compound

Product 1

HCID 677598761-Azabicyclo[3.3.1]nonane-5-carboxylic acid hydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of ethyl 1-benzyl-1-azoniabicyclo[3.3.1]-non-5-ylcarboxylate bromide (D2, 7.90 g, 0.021 mole) in ethanol (150 ml) was hydrogenated over 10% Pd/C (700mg) at atmospheric pressure and 40° C. until the uptake of hydrogen ceased. The reaction mixture was filtered through a pad of kieselguhr and the filtrate concentrated in vacuo to leave a yellow solid, which was treated with 8M hydrochloric acid (130 ml) and heated under reflux until TLC indicated that hydrolysis was complete. The solution was concentrated to dryness in vacuo to give the title compound (D14) as a yellow solid (4.8 g), which was used in the next stage without purification.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of kieselguhr
  2. concentrationthe filtrate concentrated in vacuo
  3. customto leave a yellow solid, which
  4. temperatureheated
  5. temperatureunder reflux until TLC
  6. customindicated that hydrolysis
  7. concentrationThe solution was concentrated to dryness in vacuo

Sources & evidence

ORD record
ord-b7c35f2061314a539185bec3166e07db
Source dataset
uspto-grants-1992_07
Patent number
US05132316

Reaction notes

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