Nitrogen → Tert-butyl (2-chloro-5-cyano-3-(3-oxocyclohexyl)phenyl)carbamate

Participants

Reaction Conditions

Reaction Steps

To a 20 gram dram vial was charged with tert-butyl (2-chloro-5-cyano-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamate (Example 573A)(379 mg, 1 mmol) and chloro(1,5-cyclooctadiene)rhodium(I) dimer (9.86 mg, 0.020 mmol). Dioxane (10 mL) was then added, followed by aq. KOH (2 M, 1 mL). The resulting solution was then evacuated and refilled with N2 before cyclohex-2-enone (144 mg, 1.500 mmol) was added via a syringe. The resulting reaction was heated at 80° C. for 1 h before it was cooled to room temperature. The reaction was diluted with EtOAc, washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude material was purified by flash column chromatography (0-60% EtOAc/Hexane) to give tert-butyl (2-chloro-5-cyano-3-(3-oxocyclohexyl) phenyl)carbamate (145 mg) as white foam.

Provenance & Evidence