Sodium Hydroxide → 2-(9-(tert-Butoxycarbonyl)-9-azabicyclo[3.3.1]nonan-3-yl)acetic acid

HRID 1455554Notes

Reaction equation

HRID 1455554 reaction equation
[OH-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH:15]2[CH2:16][CH2:17][CH2:18][CH:11]1[CH2:12][CH:13]([CH2:19][C:20]([O:22]CC)=[O:21])[CH2:14]2)=[O:9])([CH3:6])([CH3:5])[CH3:4]>C1COCC1.[Cl-].[Na+].O>[C:3]([O:7][C:8]([N:10]1[CH:15]2[CH2:16][CH2:17][CH2:18][CH:11]1[CH2:12][CH:13]([CH2:19][C:20]([OH:22])=[O:21])[CH2:14]2)=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 684420003-Ethoxycarbonylmethyl-9-aza-bicyclo[3.3.1]nonane-9-carboxylic acid tert-butyl ester

Product 1

HCID 574297042-(9-(tert-Butoxycarbonyl)-9-azabicyclo[3.3.1]nonan-3-yl)acetic acid

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

10 ml of 1M aqueous NaOH are added to a solution of 3-ethoxycarbonylmethyl-9-aza-bicyclo[3.3.1]nonane-9-carboxylic acid tert-butyl ester in 20 ml of THF and the mixture obtained is stirred at RT. To the mixture obtained 10 ml of brine and 70 ml of EtAc are added, and the mixture obtained is washed with 1M aqueous HCl. The organic layer obtained is dried and solvent is evaporated. 3-Carboxymethyl-9-aza-bicyclo[3.3.1]nonane-9-carboxylic acid tert-butyl ester in the form of an oil is obtained. 13C-NMR: 178.47, 177.28, 155.61, 154.50, 79.70, 79.63, 47.39, 45.88, 43.39, 40.31, 36.92, 32.22, 31.98, 31.37, 30.99, 30.74, 30.64, 30.08, 29.59, 29.20, 21.15, 20.60, 14.05.

Workup

  1. customthe mixture obtained
  2. additionare added
  3. customthe mixture obtained
  4. washis washed with 1M aqueous HCl
  5. customThe organic layer obtained
  6. customis dried
  7. customsolvent is evaporated

Sources & evidence

ORD record
ord-9e7a1af34a1244ac9f9357cbb546733a
Source dataset
uspto-grants-2009_01
Patent number
US07482462B2

Reaction notes

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