[C:1]1([C:7]2[CH:8]=[C:9]([O:14][CH2:15][C@@H:16]3[CH2:19][CH2:18][NH:17]3)[CH:10]=[N:11][C:12]=2[Cl:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C=O.[CH:22](O)=O.[BH3-]C#N.[Na+]>CCO.O.C([O-])([O-])=O.[K+].[K+]>[ClH:13].[C:1]1([C:7]2[CH:8]=[C:9]([O:14][CH2:15][C@@H:16]3[CH2:19][CH2:18][N:17]3[CH3:22])[CH:10]=[N:11][C:12]=2[Cl:13])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1To 5-phenyl-6-chloro-3-(2-(S)-azetidinylmethoxy)pyridine from Example 67 (100 mg, 0.36 mmol) in EtOH (3 mL) was added formalin (37%, 0.5 mL) and formic acid (0.25 mL), and the pH was adjusted to 6. Then NaCNBH3 (70 mg) was added, and the mixture was stirred at room temperature for 16 hours. The mixture was diluted with water and saturated with K2CO3. The mixture was extracted with CHCl3. The solvent was dried over MgSO4, filtered and concentrated. The residue was chromatographed on a silica gel column, eluting with CH2Cl2 :MeOH 10:1 to afford the free base of the title compound. MS (CI/NH3) m/z 289 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ2.05-2.14 (m, 2H), 2.40 (s, 3H), 2.32-2.44 (m, 1H), 3.34-3.51 (m, 2H), 4.44 (d, J=7.5 Hz, 2H), 7.26 (d, J=3 Hz, 1H), 8.09 (d, J=3 Hz, 1H). The salt was prepared by treatment with HCl in Et2O, as described above, to give the title compound. mp 187-188° C. MS (CNH) m/z 289 (M+H)+. 1H NMR (D2O, 300 MHz) δ2.60-2.71 (m, 2H), 2.99 (s, 3H), 3.94-4.12 (m, 1H), 4.18-4/33 (m, 1H), 4.47-4.55 (m, 3H), 7.57 (m, 5H), 7.60 (d, J=3.0 Hz, 1H), 8.18 (d, J=3.0 Hz, 1H). Anal. Calcd for C16H17N2OCl·HCl·0.5 H2O: C, 57.50; H, 5.73; N, 8.38. Found: C, 57.38; H, 5.53; N, 8.35. [α]25D=+15° (c 0.11, MeOH).
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