2-Aminocyclohex-1-ene-1-carbonitrile → 2-aminocyclohexane-1-carbonitrile
Reaction equation
[NH2:1][C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C:3]=1[C:8]#[N:9].[BH3-]C#N.[Na+]>CO.C(O)(=O)C.C(OCC)(=O)C>[NH2:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[C:8]#[N:9]Participants
6
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.
Workup
- washthe organic layer was washed with saturated NaHCO3, brine
- dry with materialdried over anhydrous Na2SO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-362529fe20684a55b771015a2944a1df
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09447039B2
Reaction notes
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