Methanol → HCID 15076313, compound

HRID 383938Notes

Reaction equation

HRID 383938 reaction equation
C([N+:8]12[CH2:14][C:11]([C:15]([O-:17])=[O:16])([CH2:12][CH2:13]1)[CH2:10][CH2:9]2)C1C=CC=CC=1.[CH3:18]O>[Pd].[C]>[N:8]12[CH2:14][C:11]([C:15]([O:17][CH3:18])=[O:16])([CH2:12][CH2:13]1)[CH2:10][CH2:9]2

Participants

4

Reactant 2

HCID 887MethanolHCID 59291333HCID 59291333, compound

Product 1

HCID 15076313HCID 15076313, compound

Reagents, catalysts & solvents 1

HCID 178418390HCID 178418390, compoundCatalyst

Procedure

To a solution of 1-benzyl-1-azoniabicyclo[2.2.1]heptane-4-carboxylate (3.25 g) in MeOH was added 10% Pd carbon with a 50% hydration (650 mg), followed by stirring at room temperature for 5 hours under a hydrogen atmosphere of 3 atm. The reaction mixture was filtered through Celite and the filtrate was concentrated. The residue was dissolved in MeOH and added with sulfuric acid (3 mL), followed by heating under reflux for 1 hour. The reaction mixture was neutralized with an aqueous K2CO3 solution and extracted with EtOAc. The organic layer was washed with water and brine in this order, dried over MgSO4, and then concentrated under reduced pressure. The residue was purified by medium-pressure preparative liquid chromatography (silica gel, YAMAZEN YFLC WPrep2XY, CHCl3: MeOH: 28% aqueous ammonia) to obtain methyl 1-azabicyclo[2.2.1]heptane-4-carboxylate (890 mg) as a colorless oily substance.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated
  3. dissolutionThe residue was dissolved in MeOH
  4. additionadded with sulfuric acid (3 mL)
  5. temperatureby heating
  6. temperatureunder reflux for 1 hour
  7. extractionextracted with EtOAc
  8. washThe organic layer was washed with water and brine in this order
  9. dry with materialdried over MgSO4
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was purified by medium-pressure preparative liquid chromatography (silica gel, YAMAZEN YFLC WPrep2XY, CHCl3: MeOH: 28% aqueous ammonia)

Sources & evidence

ORD record
ord-279964bfce23481a827cf0215dcff799
Source dataset
uspto-grants-2013_02
Patent number
US08367696B2

Reaction notes

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