Benzophenone imine → HCID 58155322, compound

Participants

Reaction Conditions

Reaction Steps

In a sealed tube a solution of (R)-5-(5-bromo-2-fluoro-phenyl)-5,6,6-trimethyl-morpholin-3-one (1.0 g, 3.2 mmol) in toluene (8 ml) was treated consecutively with sodium tert-butylate (912 mg, 9.5 mmol), 2-di-tert-butylphosphino-2′,4′,6′-triisopropylbiphenyl (tert-butyl-x-phos) (134 mg, 10 mol %) and tris(dibenzylideneacetone)-dipalladium chloroform complex [Pd2(dba)3.CHCl3] (98 mg, 5 mol %). Benzophenone imine (1.06 ml, 6.3 mmol) was added finally via syringe. The tube was sealed under argon and the mixture was stirred at 105° C. for 20 h. For the workup, the brown solution was extracted with ethyl acetate and water. The organic layer was separated, washed with brine, dried over sodium sulfate, filtered and evaporated at reduced pressure to give brown oil (1.5 g). The crude product was purified by chromatography on silica gel using a gradient of heptane and ethyl acetate=100/0 to 50/50 as the eluent. The (R)-5-[5-(benzhydrylidene-amino)-2-fluoro-phenyl]-5,6,6-trimethyl-morpholin-3-one was obtained as a light yellow foam (1.13 g, 86% of theory). Mass (calculated) C26H25FN2O2 [416.493]; (found) [M+H]+=417.

Provenance & Evidence