[C:1]([C:3]1[CH:4]=[C:5]([CH:13]=[C:14]([F:16])[CH:15]=1)[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])#[N:2].CO.O.[BH4-].[Na+]>O1CCCC1.[Co](Cl)Cl>[NH2:2][CH2:1][C:3]1[CH:4]=[C:5]([CH:13]=[C:14]([F:16])[CH:15]=1)[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7]To a mixed solution of tert-butyl 3-cyano-5-fluorobenzoate (3.00 g) in tetrahydrofuran (60.0 mL)-methanol (30.0 mL) was added a mixture of cobalt (II) chloride (4.40 g) and water (60.0 mL) under ice-cooling, and then sodium borohydride (1.54 g) was added under an argon flow, followed by stirring at room temperature for 30 minutes. The insoluble material was filtered through Celite and then washed with a mixed solvent of tetrahydrofuran-methanol-water (2:1:2, and then the filtrate was concentrated under reduced pressure. To the residue was added a saturated aqueous sodium chloride solution, followed by extraction with chloroform. The organic layer was dried over magnesium sulfate and then concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (chloroform-methanol) to obtain tert-butyl 3-(aminomethyl)-5-fluorobenzoate (1.46 g).
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