Tetrabutylammonium Hydroxide → 5-Chloro-4-[1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-4-yl]oxypyridin-2-olate;tetrabutylazanium

Participants

Reaction Conditions

Reaction Steps

A one liter round bottom flask was charged with t-butyl 4-(5-chloro-2-oxo-1,2-dihydropyridin-4-yloxy)piperidine-1-carboxylate (69.2 g, 210 mmol) and pyridine (421 mL). The slurry was heated to 80° C. until all of the material dissolved to form a clear solution. At this temperature, tetrabutylammonium hydroxide solution (152 mL, 232 mmol) was added. The mixture was concentrated in vacuo and the residual water was azeotropically removed with toluene (3×300 ml). The residue was dried under high vacuum for 12 hours to give a wet solid which was used directly in the next reaction. 1H-NMR (CDCl3, 400 MHz) δ 7.65 (s, 1H), 5.83 (s, 1H), 4.40-4.60 (m, 1H), 3.55-3.75 (m, 2H), 3.20-3.46 (m, 10H), 1.72-2.0 (m, 4H); 1.55-1.72 (m, 8H), 1.30-1.55 (m, 17H), 1.0 (t, 12H, J=7.4 Hz); Anal. Calcd for C31H56ClN3O4.0.76H2O: C, 63.76; H, 9.93; N, 7.20; Cl, 6.07. Found: C, 63.76; H, 9.87; N, 7.09; Cl, 6.21.

Provenance & Evidence