[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].[CH3:9][O:10][C:11](=[O:20])[C:12]([CH3:19])([CH3:18])[C:13](=O)[CH2:14][O:15][CH3:16].C([BH3-])#N.[Na+].C(O)(=O)C>CO.CCOC(C)=O>[CH3:9][O:10][C:11](=[O:20])[C:12]([CH3:18])([CH3:19])[CH:13]([NH:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[NH2:8])[CH2:14][O:15][CH3:16]To a mixture of 1,2-phenylenediamine (900 mg, 8.3 mmol) and 4-methoxy-2,2-dimethyl-3-oxo-butyric acid methyl ester (1.7 g, 9.8 mmol) in MeOH (5 mL) was added sodium cyanoborohydride (700 mg, 11.1 mmol) and acetic acid (1.0 mL). The mixture was stirred at room temperature for 16 hours. The reaction mixture was diluted with EtOAc (100 mL) and washed with H2O (75 mL×3). The organic layer was dried over sodium sulfate and concentrated. The resulting residue was purified by CombiFlash with 40% EtOAc in Hexane as the eluent to afford the desired 3-(2-amino-phenylamino)-4-methoxy-2,2-dimethyl-butyric acid methyl ester (550 mg, 25%).
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