Butylate → (RS)-5-[3-(benzhydrylidene-amino)-phenyl]-5-methyl-morpholin-3-one

Participants

Reaction Conditions

Reaction Steps

A dried pressure tube was charged consecutively under an argon atmosphere with a solution of (RS)-5-(3-bromo-phenyl)-5-methyl-morpholin-3-one (4.17 g, 15 mmol) in toluene (100 ml), sodium tent-butylate (4.586 g, 46 mmol), 2-di-tert-butylphosphino-2′,4′,6′-triisopropylbiphenyl (tert-butyl-x-phos) (0.675 g, 1.6 mmol), tris(dibenzylideneacetone)-dipalladium chloroform complex (0.494 g, 0.5 mmol), and benzophenone imine (5.88 g, 31 mmol). The sealed pressure tube was heated at 105° C. for 2.5 days. After cooling, the reaction mixture was evaporated to dryness and directly purified by chromatography on an Isolute flash NH2 column using a gradient of heptane/ethyl acetate=100/0 to 33/66 as the eluent. There were obtained 5.67 g (99% of theory) of (RS)-5-[3-(benzhydrylidene-amino)-phenyl]-5-methyl-morpholin-3-one as a yellow foam. Mass (calculated) C24H22N2O2 [370.455]; (found) [M+H]+=371.

Provenance & Evidence