Morpholine → 1,1-Dimethylethyl 2,3-dihydro-8-(4-morpholinyl)-1,4-benzoxazepine-4(5H)-carboxylate

Participants

Reaction Steps

A solution of tert-butyl 8-bromo-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (100 mg, 0.305 mmol), morpholine (0.0292 ml, 0.335 mmol), X-phos (8.70 mg, 0.0182 mmol), tris(dibenzylideneacetone)dipalladium(0) (5.52 mg, 0.00604 mmol) and sodium tert-butoxide (43.8 mg, 0.456 mmol) in dioxane (2 ml) was stirred under an argon atmosphere for 7 hr at 80° C. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=1:1) to give the desired product (50.0 mg, 49.0%) as an oil.

Provenance & Evidence