Ammonium Acetate → 5-Amino-cyclooctanecarbonitrile
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]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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
- customThe solvent was evaporated
- customthe residue was partitioned with dichloromethane and water
- washThe organic phase was washed with NaHCO3 solution and brine
- dry with materialdried (Na2SO4)
- filtrationfiltered
- customevaporated
- 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
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