[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]2[C:10]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17][C:11]=3[NH:12][C:13]=2[CH:14]=[CH:15][CH:16]=1.CC(C)=O.C(Cl)(Cl)Cl.[NH4+].[OH-]>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]2[C@@H:10]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17][C@H:11]3[NH:12][C:13]=2[CH:14]=[CH:15][CH:16]=1A solution of 10-(2-fluorophenyl)-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole (0.49 g, 1.74 mmol) in THF (6 mL) was added dropwise to 1.5 M borane-THF complex (6 mL, 9 mmol) and stirred at room temperature for 1.25 hours. The excess borane was quenched with H2O and the mixture was added to TFA at 0° C. After 0.3 hours the reaction was diluted with H2O and concentrated in vacuo. The residue was diluted with H2O, made basic with 15% NaOH and extracted three times with CH2Cl2. The extracts were dried over MgSO4 and concentrated in vacuo to give a white solid which was passed through a column of silica gel with 1:19 acetone/CHCl3 with 1% NH4OH to give 0.25 g (51%) of a light brown solid as the title compound: 1H NMR (400 MHz, CDCl3) δ 7.38-7.33 (m, 2 H), 7.21-7.10 (m, 3 H), 6.69 (d, J=7.7 Hz, 2 H), 3.89 (dt, J=11.0 Hz, 3.5 Hz, 1 H), 3.60-3.53 (m, 1 H), 3.18-3.12 (m, 1 H), 2.94-2.88 (m, 1 H), 2.83 (m, 1 H), 2.74-2.72 (m, 1 H), 2.21-2.16 (m, 1 H), 1.97-1.87 (m, 1 H), 1.67 (m, 1 H), 1.26 (m, 1 H); MS m/z 283.2 (M++H).
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