Cyanomethylenetributylphosphorane → HCID 89633502, compound

Participants

Reaction Conditions

Reaction Steps

To a 20 mL size microwave tube containing a stir bar was added tert-butyl (3S)-4-[2-(2,1,3-benzoxadiazol-5-yl)-2-hydroxyethyl]-3-(hydroxymethyl)piperazine-1-carboxylate (0.80 g, 2.1 mmol), cyanomethylene tri-n-Butylphosphorane (0.92 g, 3.8 mmol) and anhydrous toluene (15 mL). The tube was degassed and purged with N2 followed by heating at 100° C. for 12 h. The solution was concentrated to dryness and the organic residue was then purified over silica gel with the solvent systems of 30% Acetone in DCM to furnish the title compound: 1H-NMR (CDCl3, 500 MHz), δ 7.854-7.832 (m, 2H), 7.428 (d, J=9 Hz, 1H), 4.754 (d, J=10.5 Hz, 1H), 4.041-4.015 (m, 3H), 3.774-3.733 (m, 2H), 3.517 (t, J=11 Hz, 1H), 3.011 (d, J=11.5 Hz, 1H), 2.782 (d, J=9.5 Hz, 1H), 2.335-2.240 (m, 3H), 1.510 (s, 9H).

Provenance & Evidence