HCID 11311485, compound → HCID 10612438, compound

HRID 1409047Notes

Reaction equation

HRID 1409047 reaction equation
C1([C:7]([N:9]2[CH:13]3[CH2:14][CH2:15][C:10]2([C:16]([O:18]C)=[O:17])[CH2:11][CH2:12]3)=[O:8])C=CC=CC=1>Cl>[CH2:16]([O:17][C:7]([N:9]1[CH:13]2[CH2:12][CH2:11][C:10]1([C:16]([OH:18])=[O:17])[CH2:15][CH2:14]2)=[O:8])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

3

Reactant 1

HCID 11311485HCID 11311485, compound

Product 1

HCID 10612438HCID 10612438, compoundYield 57.7%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of methyl 7-(phenylcarbonyl)-7-azabicyclo[2.2.1]heptane-1-carboxylate (8.0 g) produced above and concentrated hydrochloric acid (100 mL) was heated under reflux for 24 hr, and concentrated under reduced pressure. To the residue was added water (50 mL), and the mixture was washed twice with ethyl acetate. To the obtained aqueous layer was basified with sodium carbonate, a solution of sodium carbonate (9.80 g) and benzylchlorocarbonate (5.40 mL) in 1,4-dioxane (30 mL), and the mixture was stirred at room temperature overnight. The reaction mixture was washed twice with ethyl acetate, and the aqueous layer was adjusted to pH3 with 2M hydrochloric acid. The organic product was extracted 3 times with ethyl acetate (150 mL), and the combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give the title compound (2.45 g) as a yellow solid.

Workup

  1. customproduced above
  2. temperatureunder reflux for 24 hr
  3. concentrationconcentrated under reduced pressure
  4. additionTo the residue was added water (50 mL)
  5. washthe mixture was washed twice with ethyl acetate
  6. washThe reaction mixture was washed twice with ethyl acetate
  7. extractionThe organic product was extracted 3 times with ethyl acetate (150 mL)
  8. washthe combined organic layers were washed with brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-719689b1fb6948c592fcdf9647f9c1db
Source dataset
uspto-grants-2014_12
Patent number
US08921354B2

Reaction notes

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