9-Benzoylamino bicyclo[3.3.1]nonane-9-carboxylic acid → 9-aminobicyclo[3.3.1]nonane-9-carboxylic Acid

HRID 1040337Notes

Reaction equation

HRID 1040337 reaction equation
C([NH:9][C:10]1([C:19]([OH:21])=[O:20])[CH:15]2[CH2:16][CH2:17][CH2:18][CH:11]1[CH2:12][CH2:13][CH2:14]2)(=O)C1C=CC=CC=1>CC(O)=O.Cl>[NH2:9][C:10]1([C:19]([OH:21])=[O:20])[CH:15]2[CH2:16][CH2:17][CH2:18][CH:11]1[CH2:12][CH2:13][CH2:14]2

Participants

4

Reactant 1

HCID 667207679-Benzoylamino bicyclo[3.3.1]nonane-9-carboxylic acid

Product 1

HCID 48666329-aminobicyclo[3.3.1]nonane-9-carboxylic AcidYield 98.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Procedure

Dissolve 3 g (10.44 mmol) of 9-benzoylamino bicyclo[3.3.1]nonane-9-carboxylic acid in 200 mL of AcOH and 50 mL of 6N HCl aqueous solution, reflux the mixture for 18 h and then concentrate partially by distillation of 150 mL of solvent. After cooling, filter the reaction mixture and distribute in 150 mL of a 1:2 mixture of 1N HCl aqueous solution/ether. After extraction, concentrate the aqueous phase and then treat it dropwise with a 12N aqueous solution of soda (NaOH) to adjust the pH to 5-6. Filter the amino acid thus precipitated, wash with 3×50 mL of water and dry under reduced pressure, which gives 1.88 g of 9-aminobicyclo[3.3.1]nonane-9-carboxylic acid in the form of white crystals.

Workup

  1. temperaturereflux the mixture for 18 h
  2. concentrationconcentrate partially by distillation of 150 mL of solvent
  3. temperatureAfter cooling
  4. filtrationfilter the reaction mixture
  5. additiondistribute in 150 mL of a 1:2 mixture of 1N HCl aqueous solution/ether
  6. extractionAfter extraction
  7. concentrationconcentrate the aqueous phase
  8. additiontreat it dropwise with a 12N aqueous solution of soda (NaOH)
  9. filtrationFilter the amino acid
  10. customthus precipitated
  11. washwash with 3×50 mL of water
  12. customdry under reduced pressure, which

Sources & evidence

ORD record
ord-3e10d4f716024efea54bfb66ce65614b
Source dataset
uspto-grants-2013_10
Patent number
US08552201B2

Reaction notes

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