Triphenylphosphine → HCID 86675415, compound

Participants

Reaction Steps

Ozone was bubbled through a solution of methyl 4-[bis(tert-butoxycarbonyl)amino]6-ethenyl-3-methoxypyridine-2-carboxylate (0.382 g, 0.935 mmol) in CH2Cl2 (9.35 ml) at −78° C. until the solution turned blue. Oxygen was bubbled through the reaction mixture until the solution turned yellow and triphenylphosphine (0.294 g, 1.122 mmol) was added. The reaction mixture was allowed to warm to room temperature and was stirred overnight. The reaction mixture was then adsorbed onto celite and the residue was purified by flash column chromatography (ISCO, SiO2 24 g, hexanes/EtOAc 100:0 to 0:100 gradient) to afford methyl 4-[bis(tert-butoxycarbonyl)amino]-6-formyl-3-methoxypyridine-2-carboxylate (279 mg, 0.680 mmol, 72.7% yield) as a light yellow oil. ESIMS m/z 411 ([M−H]+); 1H NMR (400 MHz, CDCl3) δ 10.03 (s, 1H), 7.88 (s, 1H), 4.05 (s, 3H), 3.95 (s, 3H), 1.43 (s, 18H).

Provenance & Evidence