Diethyl (cyanomethyl)phosphonate → HCID 67451704, compound

Participants

Reaction Conditions

Reaction Steps

Diethyl cyanomethylphosphonate (4.247 mL, 26.99 mmol) was suspended in THF (135.0 mL) and cooled to 0° C. Potassium 2-methylpropan-2-olate (32.39 mL, 32.39 mmol) was added portion-wise and stirred at 0° C. for 10 minutes. tert-Butyl 3-oxopyrrolidine-1-carboxylate (5 g, 26.99 mmol) was added dropwise as a solution in THF (25 mL). The resulting mixture was allowed to warm to ambient temperature overnight. The reaction mixture was concentrated under reduced pressure and the residue partitioned between saturated aqueous NH4Cl and EtOAc. The organics were washed with brine, dried, MgSO4 and concentrated under reduced pressure to afford the crude material, which was passed through a pad of Celite® and silica, eluting with DCM to furnish tert-butyl 3-(cyanomethylene)pyrrolidine-1-carboxylate (2.5 g, 12.00 mmol, 44.47% yield. 1H NMR (CDCl3) δ 5.8 (s, 1H), 4.26 (t, 2H), 3.85 (s, 2H), 2.28 (t, 2H), 2.06-1.96 (m, 1H), 1.54 (s, 9H).

Provenance & Evidence