2-Aminocyclohex-1-ene-1-carbonitrile → 2-aminocyclohexane-1-carbonitrile

HRID 62657Notes

Reaction equation

HRID 62657 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

Reactant 2

HCID 2901752-Aminocyclohex-1-ene-1-carbonitrileHCID 5003444Sodium cyanoborohydride

Product 1

HCID 211638632-aminocyclohexane-1-carbonitrileYield 78.6%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

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

  1. washthe organic layer was washed with saturated NaHCO3, brine
  2. dry with materialdried over anhydrous Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-362529fe20684a55b771015a2944a1df
Source dataset
uspto-grants-2016_09
Patent number
US09447039B2

Reaction notes

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