Cis-2-boc-hexahydropyrrolo[3,4-C]pyrrole → HCID 44469278, compound

Participants

Reaction Steps

A solution of sodium tert-butoxide (98 mg, 1.017 mmol) and (3aR,6aS)-tert-butyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate (95 mg, 0.436 mmol) in THF (3 mL) was stirred under nitrogen. To this was added 1,1′-bis(diphenylphosphino)ferrocene (25 mg, 0.05 mmol), Pd2(DBA)3 (12 mg, 0.02 mmol) and 1-(7-bromoquinolin-4-yl)-3-(pyrazin-2-yl)urea (100 mg, 0.291 mmol). The mixture was then heated at reflux for 12 h before partitioning between CH2Cl2 and water. The mixture was filtered through Celite and the organic phase was separated. The water phase was extracted twice with CH2Cl2 and the combined extracts dried (Na2SO4), filtered and concentrated in vacuo to provide the crude material, which was purified by flash chromatography to give the title compound (127 mg, 83%) as a white solid.

Provenance & Evidence