[CH:1]([N:4]([CH:7]([CH3:9])C)[CH2:5][CH3:6])([CH3:3])C.ClC1C=[CH:17][C:14]([C:15]#[N:16])=[CH:13][N:12]=1.[C:19]([O:23][C:24](C1CCNC1)=[O:25])([CH3:22])([CH3:21])[CH3:20].C[N:32](C=O)C>ClCCl>[C:19]([O:23][C:24](=[O:25])[NH:32][CH:9]1[CH2:6][CH2:5][N:4]([C:1]2[CH:3]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][N:12]=2)[CH2:7]1)([CH3:22])([CH3:21])[CH3:20]
Stir a solution of diisopropylethylamine (9.5 mL, 54.3 mmol), 6-chloronicotinonitrile (5 g, 36.2 mmol) and 3-tert-butyloxycarbonylpyrrolidine (10 g, 54.3 mmol) in DMF (10 mL). After 3 days, dilute with dichloromethane and an aqueous saturated solution of sodium bicarbonate and separate the layers. Extract the aqueous layer once with dichloromethane, dry (sodium sulfate), filter and concentrate. Filter through a plug of silica gel, wash with dichloromethane and concentrate to give [1-(5-cyanopyridin-2-yl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester as a white solid (8.13 g, 78%). 1H NMR (400 MHz, CDCl3) δ 8.38 (dd, 1H, J=2.4 Hz, 1.0 Hz), 7.58-7.55 (m, 1H), 6.33 (dd, 1H, J=9.8 Hz, 1.0 Hz), 4.85-4.7 (m, 1H), 4.40-4.25 (m, 1H), 3.85-3.30 (m, 4H), 2.35-2.25 (m, 1H), 2.08-1.90 (m, 1H), 1.43 (s, 9H); MS (ES): m/z=289 [M+H]+.
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