Pyrrolidine → 1,1-Dimethylethyl 2,3-dihydro-9-(1-pyrrolidinyl)-1,4-benzoxazepine-4(5H)-carboxylate

Participants

Reaction Steps

A solution of tert-butyl 9-bromo-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (350 mg, 1.07 mmol), pyrrolidine (0.274 ml, 3.27 mmol), X-phos (30.5 mg, 0.064 mmol), tris(dibenzylideneacetone)dipalladium(0) (19.3 mg, 0.0212 mmol) and sodium tert-butoxide (154 mg, 1.60 mmol) in dioxane (7 ml) was stirred under an argon atmosphere for 2 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 and the residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=3:1) to give the desired product (90.0 mg, 26.4%) as an oil.

Provenance & Evidence