1,4-Dioxane → HCID 68539560, compound

Participants

Reaction Steps

Pd(dba)2 (0.068 g, 0.109 mmol), rac-BINAP (0.078 g, 0.085 ml) and sodium tert-butoxide (0.22 g, 2.28 mmol) were combined into a pressure flask. To the reaction mixture was then added dry 1,4-dioxane (3 mL) under nitrogen and the resulting mixture stirred for 1 minute. To the reaction mixture was then added, under nitrogen, a solution of 4-{(2-bromo-phenyl)-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-carbamoyl}-piperidine-1-carboxylic acid tert-butyl ester (0.78 g, 1.52 mmol) in dry 1,4-dioxane (9 mL). The pressure flask was sealed and degassed under high vacuum and left under nitrogen. The reaction mixture was stirred at 110° C. for 6 hours and then partitioned with aqueous 0.5 M citric acid, water and methylene chloride. The organic layer was washed with brine, dried with Na2SO4, filtered and the solvent evaporated in vacuo to yield a solid. The solid was purified via flash chromatography (50% ethyl acetate/hexanes) to yield the title compound as a foam.

Provenance & Evidence