Reaction #90935

Reaction equation

2-aminocyclohex-1-enecarbonitrile

NaCNBH3

→

diastereomeric mixture

Yield 78.6%

2-Aminocyclohexanecarbonitrile

Yield 78.6%

Solvents

methanol

ethyl acetate

Conditions

Workup

1. 1
   Washthe organic layer was washed with saturated NaHCO3, brine
2. 2
   Dryingdried over anhydrous Na2SO4
3. 3
   Concentrationconcentrated

Procedure

To a cold solution of 2-aminocyclohex-1-enecarbonitrile (I-7a: 50 mg, 0.41 mmol) in methanol (3 mL) was added NaCNBH3 (103 mg, 1.64 mmol) and acetic acid (5 drops) at 0° C. The resulting mixture was stirred at room temperature for 16h. The reaction mixture was diluted with ethyl acetate and the organic layer was washed with saturated NaHCO3, brine, dried over anhydrous Na2SO4 and concentrated to afford 40 mg (78%) of diastereomeric mixture of 2-aminocyclohexanecarbonitrile (I-7b) as a gum.

Source