Ammonium Chloride → (3,5-Difluoropyridin-2-YL)methanol
反応式
C([O:3][C:4]([C:6]1[C:11]([F:12])=[CH:10][C:9]([F:13])=[CH:8][N:7]=1)=O)C.[BH4-].[Na+].[Cl-].[NH4+]>C(O)C>[F:12][C:11]1[C:6]([CH2:4][OH:3])=[N:7][CH:8]=[C:9]([F:13])[CH:10]=1C([O:3][C:4]([C:6]1[C:11]([F:12])=[CH:10][C:9]([F:13])=[CH:8][N:7]=1)=O)C.[BH4-].[Na+].[Cl-].[NH4+]>C(O)C>[F:12][C:11]1[C:6]([CH2:4][OH:3])=[N:7][CH:8]=[C:9]([F:13])[CH:10]=1To a solution of 3,5-difluoro-pyridine-2-carboxylic acid ethyl ester of Step A (2.5 g, 12.6 mmol) in ethanol (10 mL), cooled using an ice water bath, was added sodium borohydride (1.43 g, 37.8 mmol) in a portion wise manner. The solution was stirred at 0° C. for thirty minutes and at ambient temperature for two hours. The reaction was returned to 0° C. and saturated ammonium chloride was added dropwise. The solvent was removed in vacuo and the resulting residue was partitioned between ethyl acetate and water. The organic layer was washed with saturated ammonium chloride, water and brine and dried over magnesium sulfate. The slurry was filtered and concentrated to provide the alcohol as a yellow oil (1.8 g, 98%). MS (M+H): 146
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