GENERAL METHODS: N-Boc-L-prolinamide (5 g, 23.3 mmol) and cyanuric chloride (2.58 g, 14.0 mmol) were dissolved in DMF (10 mL), and the reaction was stirred at room temperature for 1 h (the reaction progress was monitored by TLC). After completion of the reaction, the reaction mixture was extracted with EtOAc, the organic phase was washed sequentially with water and saturated saline, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography with petroleum ether/ethyl acetate (1/1, v/v) as eluent to afford (S)-1-N-Boc-2-pyrrolidinecarbonitrile (3.48 g, 76% yield) as a white solid.1H NMR (300 MHz, CDCl3) δ 4.76 (s, 1H), 3.51 (s, 2H), 2.34-2.31 (m 1H), 2.17-2.10 (m, 2H), 1.90-1.87 (m, 1H), 1.49 (s, 9H).MS (ESI) m/z 197 [M + H]+.
