[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:11][CH2:10][NH:9][CH2:8][C@H:7]([CH3:12])[C:6]=2[C:13]=1[Cl:14].[C:15](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C=O>ClC(Cl)C.[OH-].[Na+]>[CH3:15][N:9]1[CH2:8][C@H:7]([CH3:12])[C:6]2[C:13]([Cl:14])=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[CH2:11][CH2:10]1A solution of (R)-8,9-dichloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine (0.05 g, 0.20 mmol) in dichloroethane (3 mL) was treated with sodium triacetoxyborohydride (0.073 g, 0.35 mmol) and formaldehyde (0.017 mL, 37% solution in water). This was stirred at 20° C. for 2 h. The reaction was diluted with 15% NaOH and extracted with ethyl acetate (2×10 mL). The organics were dried with MgSO4, filtered and concentrated to give 0.042 g as an oil. 1H NMR (400 MHz, CDCl3) δ 7.19 (d, J=8 Hz, 1H), 6.89 (d, J=8 Hz, 1H), 3.91-3.88 (m, 1H), 3.28 (ddd, J=15, 12, 2 Hz, 1H), 2.99-2.88 (m, 2H), 2.68 (ddd, J=15, 5, 1 Hz, 1H), 2.36-2.32 (m, 4H), 2.13 (t, J=11 Hz, 1H), 1.27 (d, J=7 Hz, 3H). MS calculated for C12H15Cl2N+H: 243, observed: 243.
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