Sodium Cyanide → Benzyl 3-cyanopyrrolidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of 13.4 g (35.7 mmol) of benzyl 3-(p-methylbenzenesulfonyloxy)pyrrolidine-1-carboxylate in 49 mL of DMSO were added 2.58 g (50.6 mmol) of finely powdered sodium cyanide. The reaction mixture was heated at 80° C. for 3.5 hours and then cooled to room temperature. The crude was diluted with 100 mL of brine and extracted with diethyl ether (5×250 mL). The extracts were combined, washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was chromatographed on silica gel with 60% ethyl acetate/hexanes to give 6.8 g (83%) of benzyl 3-cyanopyrrolidine-1-carboxylate as a clear oil. Rf=0.46 in 100% ethyl acetate; Mass Spectrum (FD+): M+=230; IR (CHCl3, cm-1): 882, 912, 986, 1030, 1119, 1169, 1292, 1347, 1362, 1424, 1451, 1468, 1486, 1498, 1702, 2891, 2962, 3021; UV (C2H5OH) λmax =206 (ε=9299), 258 (ε=214); Anal. Calcd. for C13 H14N2O2 : C,67.81; H,6.13; N,12.17; Found: C, 67.58; H. 6.26; N, 12.43; 1H NMR (300 MHz, CDC13) δ2.25-2.31 (m, 2H); 3.11 (t, J=6.5 Hz, 1H); 3.48-3.75 (m, 3H); 5.15 (s, 2H); 7.37 (s, 5H).

Provenance & Evidence