Ammonium Acetate → 5-Amino-cyclooctanecarbonitrile

HRID 16230Notes

Reaction equation

HRID 16230 reaction equation
O=[C:2]1[CH2:9][CH2:8][CH2:7][CH:6]([C:10]#[N:11])[CH2:5][CH2:4][CH2:3]1.C([O-])(=O)C.[NH4+].C([BH3-])#[N:18].[Na+]>CO>[NH2:18][CH:2]1[CH2:9][CH2:8][CH2:7][CH:6]([C:10]#[N:11])[CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 66656982HCID 66656982, compound

Product 1

HCID 666569845-Amino-cyclooctanecarbonitrile

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The product of Example 10B (0.259 g, 1.71 mmol), ammonium acetate (1.32 g, 17.14 mmol), and sodium cyanoborohydride (0.43 g, 6.84 mmol) was stirred in methanol (8 mL) for twelve hours. The solvent was evaporated and the residue was partitioned with dichloromethane and water. The organic phase was washed with NaHCO3 solution and brine, dried (Na2SO4), filtered, and evaporated. The crude title compound was used in the following step without further purification.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was partitioned with dichloromethane and water
  3. washThe organic phase was washed with NaHCO3 solution and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude title compound was used in the following step without further purification

Sources & evidence

ORD record
ord-329e3ec9dae6413cb347606bd05c3108
Source dataset
uspto-grants-2010_06
Patent number
US07737137B2

Reaction notes

Loading…