Pyridine 2-aldoxime → HCID 67284112, compound

Participants

Reaction Steps

Sodium hypochlorite (16 ml of a 14% w/v aqueous solution, 29.5 mmol) was added dropwise to a solution of 2-pyridinealdoxime (2 g, 16.4 mmol) and N-tert-butoxycarbonyl-propargylamine (5.6 g, 36.1 mmol) in DCM (30 ml) cooled in an ice bath. The mixture was stirred vigorously and allowed to warm to ambient temperature and stirred for 18 hours. The aqueous layer was separated and extracted with DCM. The combined organic extracts were combined, dried (MgSO4) and the solvent removed by evaporation. The residue was purified by column chromatography on silica gel eluting with diethyl ether/isohexane (1:1) to give the title compound (1.93 g, 43%). NMR (CDCl3) 1.45 (s, 9H), 4.5 (m, 2H), 5.03 (bs, 1H), 6.8 (s, 1H), 7.35 (m, 1H), 7.8 (m, 1H), 8.05 (d, 1H), 8.67 (m, 1H).

Provenance & Evidence