[CH3:1][C:2]1[C:7]([CH2:8][N:9]=CC2C(=O)C3C(C)(C)C2(C)CC3)=[CH:6][C:5]([C:22]([CH3:24])=[CH2:23])=[CH:4][N:3]=1.[BH4-].[Na+].Cl>CCO>[CH:22]([C:5]1[CH:6]=[C:7]([CH2:8][NH2:9])[C:2]([CH3:1])=[N:3][CH:4]=1)([CH3:24])[CH3:23]To a stirring solution of 96.6 mg (0.370 mmol) of 1-(2-methyl-5-(prop-1-en-2-yl)pyridin-3-yl)-N-((oxobornyl)methylene)methanamine and 88.5 mg (0.372 mmol) of CoCl2.6H2O in 4 mL of EtOH at 50° C. was added 160 mg of NaBH4 in 2 portions. After heating the mixture at 50° C. under Ar for 5 h, the reaction mixture was cooled and 5 N HCl was added to a pH=1. The mixture was stirred at r.t. for 15 h and concentrated. Water was added, and NH4OH was added to a pH=9. The aqueous layer was extracted with the extract of (40 mL of CHCl3: 5 mL of MeOH: 5 mL H2O) (2×). The combined extracts were dried over Na2SO4, filtered, and concentrated. (5-isopropyl-2-methylpyridin-3-yl)methanamine was used in the next reaction without further purification.
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