[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][NH:4][CH:3]1[C:8]1[O:12][N:11]=[C:10]([C:13]2[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=2)[C:16]#[N:17])[N:9]=1.[N:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH:27]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[CH3:1][C@H:2]1[CH2:7][CH2:6][CH2:5][N:4]([CH2:27][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][N:21]=2)[C@H:3]1[C:8]1[O:12][N:11]=[C:10]([C:13]2[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=2)[C:16]#[N:17])[N:9]=1The reaction was carried out as described in Example 43 from 3-[5-(3-methyl-piperidin-2-yl)-[1,2,4]oxadiazol-3-yl]-benzonitrile (29 mg, 0.108 mmol) with pyridine-2-carbaldehyde (13.9 mg, 0.13 mmol) and sodium triacetoxyborohydride (34.3 mg, 0.162 mmol) in dichloroethane (2 mL) to give cis-3-[5-(3-Methyl-1-pyridin-2-ylmethyl-piperidin-2-yl)-[1,2,4]oxadiazol-3-yl]-benzonitrile (20 mg, 51.5%); 1H NMR (CDCl3), δ(ppm): 8.55 (d,1H), 8.45 (s, 1H), 8.38 (d, 1H), 7.80 (d,1H), 7.65 (m, 2H), 7.41 (d, 1H), 7.18(m, 1H), 4.40 (d, 1H), 3.76 (d, 1H), 3.53 (d, 1H), 3.03 (m,1H), 2.68 (m,1H), 2.30 (m, 1H), 1.74(m, 4H), 0.82 (d, 3H); and trans-3-[5-(3-methyl-1-pyridin-2-ylmethyl-piperidin-2-yl)-[1,2,4]oxadiazol-3-yl]-benzonitrile (5 mg, 12.9%); 1H NMR (CDCl3), δ(ppm): 8.49+ (d,1H), 8.43 (s, 1H), 8.35 (d, 1H), 7.80 (d,1H), 7.65 (m, 2H), 7.55 (d, 1H), 7.14(m, 1H), 3.59 (m, 3H), 3.03 (m, 1H), 2.25 (m, 2H), 1.92 (m,1H), 1.73 (m, 2H), 1.27(m, 1H), 0.87 (d, 3H).
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