[CH2:1]([N:8]=[C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([F:18])[CH:16]=2)[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].ClCCl.O>C(O)C>[CH2:1]([NH:8][CH:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([F:18])[CH:16]=2)[CH2:11][CH2:10]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Dissolve benzyl-(6-fluoroindan-1-ylidene)-amine (23.22 g, 97.03 mmol) in ethanol (1200 mL). Cool the mixture to 0° C. under nitrogen. Add sodium borohydride (11.01 g, 291.10 mmol) to the mixture. After one hour, add dichloromethane (150 mL) and water (150 mL). Stir for 14 hours under nitrogen and concentrate in vacuo to remove ethanol. Extract the residue with dichloromethane and saturated aqueous sodium chloride. Dry the resulting organics with magnesium sulfate, filter, and concentrate in vacuo to give the title compound as a red oil (22.12 g, 94%). MS (ES) m/z=242 [M+1].
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