Cesium carbonate → HCID 71003668, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of tert-butyl 2-((R)-1-azetidin-2-ylmethoxy)-6-benzyloxycarbonylamino-3-bromo-benzoate (Intermediate 46, 1.46 g), palladium acetate (0.167 g), cesium carbonate (1.935 g) and 2,2′-bis(diphenylphosphino)-1,1′-binaphthalene (0.925 g) in toluene (35 mL) was stirred and heated at 100° C. under nitrogen for 4 hours. After cooling, the mixture was diluted with ethyl acetate and water and filtered through celite. The organic layer was separated, dried (Na2SO4) and filtered and the filtrate was concentrated in vacuo. The residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 5-40% to give tert-butyl (R)-6-benzyloxycarbonylamino-1,2,2a,3-tetrahydro-4-oxa-8b-azacyclobuta[a]naphthalene-5-carboxylate (0.141 g) as an off-white solid.

Provenance & Evidence