Sodium Hydroxide → HCID 19887591, compound

HRID 383935Notes

Reaction equation

HRID 383935 reaction equation
CC1C=CC(S([O-])(=O)=O)=CC=1.C([N+:19]12[CH2:26][C:23]([OH:27])([CH2:24][CH2:25]1)[CH2:22][CH2:21][CH2:20]2)C1C=CC=CC=1.C([O-])=O.[NH4+].[OH-].[Na+]>[Pd].[C].CCO>[N:19]12[CH2:26][C:23]([OH:27])([CH2:24][CH2:25]1)[CH2:22][CH2:21][CH2:20]2

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 2723923Ammonium formateHCID 86641065HCID 86641065, compound

Product 1

HCID 19887591HCID 19887591, compoundYield 68.9%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To 1-benzyl-5-hydroxy-1-azoniabicyclo[3.2.1]octane 4-methylbenzenesulfonate (800 mg) that had been synthesized by the method as described in Published Japanese Patent Application No. 63-290878 was added a mixture of EtOH (8 mL), 10% Pd/Carbon with a 50% hydration (200 mg), and ammonium formate (500 mg), followed by heating under reflux. The reaction mixture was alkalified with addition of a 1 M aqueous NaOH solution, and extracted with a mixed solvent (CHCl3:MeOH=9:1). The organic layer was dried over MgSO4 and then concentrated under reduced pressure to obtain 1-azabicyclo[3.2.1]octan-5-ol (180 mg) as a colorless oily substance.

Workup

  1. addition63-290878 was added
  2. temperatureby heating
  3. temperatureunder reflux
  4. extractionextracted with a mixed solvent (CHCl3:MeOH=9:1)
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c0f2379a4a984ec1aa41bf6b2f7e2ed5
Source dataset
uspto-grants-2013_02
Patent number
US08367696B2

Reaction notes

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