B.O1CCCC1.[C:7]1([CH:13]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:14]2[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][C:22]#[N:23])[CH2:16][CH2:15]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Cl.[OH-].[Na+]>>[NH2:23][CH2:22][CH2:21][CH2:20][N:17]1[CH2:18][CH2:19][CH:14]([CH:13]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:15][CH2:16]1Borane-tetrahydrofuran complex (1.0 M in THF, 5.5 mL, 5.5 mmol, 3.5 equiv) was added under argon to neat 3-(4-diphenylmethylpiperidin-1-yl)propionitrile (480 mg, 1.58 mmol, 1.00 equiv). The mixture was stirred at reflux for 5 hours and then cooled to 0° C. Aqueous HCl (6 N, 6 mL) was added cautiously, and stirring was continued at room temperature overnight, then at 42° C. for 1.5 hours. The solution was basified to pH 10-11 by addition of 6 N aqueous NaOH and extracted with CH2Cl2 (3×50 mL). The combined organic solutions were dried over MgSO4 and concentrated. The residue was purified by flash chromatography (SiO2, CHCl3-MeOH-NH3 (2.0 M in MeOH) to give 420 mg (86%) of colorless oil, which was characterized spectroscopically.
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