Ammonium Acetate → 9-Amino-bicyclo[3.3.1]nonane-3-carboxylic acid methyl ester

HRID 16220Notes

Reaction equation

HRID 16220 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:12][CH:11]2[C:13](=O)[CH:7]([CH2:8][CH2:9][CH2:10]2)[CH2:6]1)=[O:4].C([O-])(=O)C.[NH4+].[BH3-]C#[N:22].[Na+]>CO>[CH3:1][O:2][C:3]([CH:5]1[CH2:12][CH:11]2[CH:13]([NH2:22])[CH:7]([CH2:8][CH2:9][CH2:10]2)[CH2:6]1)=[O:4]

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 19245419Methyl 9-oxobicyclo[3.3.1]nonane-3-carboxylate

Product 1

HCID 666569239-Amino-bicyclo[3.3.1]nonane-3-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The product of Example 7A (2.03 g, 10.38 mmol) was stirred at room temperature in the presence of ammonium acetate (8 g, 103.8 mmol) and NaBH3CN (3.3 g, 51.9 mmol) in methanol (30 mL) for twelve hours at 23° C. The solvent was then evaporated and the residue was dissolved in dichloromethane; washed with water, NaHCO3 solution, and brine; and dried (Na2SO4). After filtration and evaporation of the solvent, the amine was used without further purification.

Workup

  1. customThe solvent was then evaporated
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washwashed with water, NaHCO3 solution, and brine
  4. dry with materialand dried (Na2SO4)
  5. filtrationAfter filtration and evaporation of the solvent
  6. customthe amine was used without further purification

Sources & evidence

ORD record
ord-4caae9e1348f4abdab29fcccbc4f0030
Source dataset
uspto-grants-2010_06
Patent number
US07737137B2

Reaction notes

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