[C:1]([C:5]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][C:6]=1[C:7]#[N:8])([CH3:4])([CH3:3])[CH3:2].B.C1COCC1.CO.Cl>C1COCC1.O>[C:1]([C:5]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][C:6]=1[CH2:7][NH2:8])([CH3:4])([CH3:2])[CH3:3]To a solution of 2-tert-butyl-5-nitrobenzonitrile (612 mg, 3.0 mmol) in THF (10 mL) was added a solution of BH3.THF (12 mL, 1M in THF, 12.0 mmol) under nitrogen. The reaction mixture was stirred at 70° C. overnight and cooled to 0° C. Methanol (2 mL) was added followed by the addition of 1N HCl (2 mL). After refluxing for 30 min, the solution was diluted with water and extracted with EtOAc. The aqueous layer was basified with 1N NaOH and extracted with EtOAc twice. The combined organic layers were washed with brine and dried over Mg2SO4. After removal of solvent, the residue was purified by column chromatography (0-10% MeOH—CH2Cl2) to give (2-tert-butyl-5-nitrophenyl)methanamine (268 mg, 43%). 1H NMR (400 MHz, DMSO-d6) δ 8.54 (d, J=2.7 Hz, 1H), 7.99 (dd, J=8.8, 2.8 Hz, 1H), 7.58 (d, J=8.8 Hz, 1H), 4.03 (s, 2H), 2.00 (t, J=2.1 Hz, 2H), 1.40 (s, 9H); HPLC ret. time 2.05 min, 10-100% CH3CN, 5 min gradient; ESI-MS 209.3 m/z (MH+).
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