[F:1][C:2]1[CH:10]=[CH:9][C:8]2[C:7](=[CH2:11])[CH2:6][CH2:5][C:4]=2[C:3]=1[C:12]#[N:13].[O:14]1CCCC1.B.OO.[OH-].[Na+]>C1COCC1.CCOC(C)=O>[F:1][C:2]1[CH:10]=[CH:9][C:8]2[CH:7]([CH2:11][OH:14])[CH2:6][CH2:5][C:4]=2[C:3]=1[C:12]#[N:13]5-Fluoro-1-methylidene-2,3-dihydro-1H-indene-4-carbonitrile (100 mg, 0.577 mmol) in THF (6 mL) at 0° C. was treated with borane tetrahydrofuran (1 M, 0.751 ml, 0.751 mmol). The resulting mixture was stirred for overnight at room temperature; LC analysis indicated consumption of starting material. To the mixture was added a combination of hydrogen peroxide (0.083 ml, 0.81 mmol) and 2M NaOH (0.404 ml, 0.808 mmol). The resulting mixture was then stirred for 2 hours. LC analysis indicated completion of the reaction. The reaction mixture was diluted with EtOAc, washed with brine, dried over Na2SO4, filtered and concentrated to dryness. The residue was absorbed into silica gel and loaded into silica column for separation with the solvent systems of hexanes/EtOAc (1/1) to give the desired product 5-fluoro-1-(hydroxymethyl)-2,3-dihydro-1H-indene-4-carbonitrile.
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