[C:1]([CH:3]1[CH2:8][CH2:7][C:6](=O)[CH2:5][CH2:4]1)#[N:2].[CH3:10][NH2:11].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C1COCC1.C(Cl)Cl>[CH3:10][NH:11][CH:6]1[CH2:7][CH2:8][CH:3]([C:1]#[N:2])[CH2:4][CH2:5]1To a solution of 4-cyanocyclohexanone (200 mg, 1.626 mmol) and CH3NH2 (2M in THF) (0.8 mL, 1.626 mmol) in THF:CH2Cl2 (1:1) (4.0 mL) at 0° C. was added NaBH(OAc)3 (689 mg, 3.252 mmol) and the resulting mixture was stirred at rt for 48 h. Subsequently, the solvent was removed under reduced pressure and the residue was dissolved in ethyl acetate, washed with water, brine, dried over Na2SO4 and concentrated to afford 200 mg (89%) of 4-(methylamino)cyclohexanecarbonitrile as a white solid. 1H NMR (400 MHz, DMSO-d6) 2.91 & 2.61 (two signals, 1H) 2.23-2.24 (m, 3H) 1.02-1.99 (m, 9H); ELSD/MS (Method 3) (m/z): [M+H]+ 139.06.
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