Cesium carbonate → tert-Butyl 5-(5-ethoxycarbonylpyridin-3-yl)hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate

Participants

Reaction Steps

A suspension of tert-butyl hexahydropyrrolo[3,4-c]pyrrole-2(1 H)-carboxylate (2.00 g, 9.42 mmol; see Schrimpf, Michael R.; Tietje, Karin R.; Toupence, Richard B.; Ji, Jianguo; Basha, Anwer; Bunnelle, William H.; Daanen, Jerome F.; Pace, Jennifer M.; Sippy, Kevin B. WO 2001081347), ethyl 5-bromonicotinate (2.80 g, 12.0 mmol; Aldrich), tris(dibenzylideneacetone)dipalladium(0) (259 mg, 0.283 mmol; Strem), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (491 mg, 0.848 mmol; Aldrich) and cesium carbonate (4.91 g, 15.1 mmol; Aldrich) in anhydrous dioxane (50 mL) was heated at 90° C. for 72 hours. The reaction mixture was cooled and filtered through a glass frit. The filtrate was concentrated and the residue was purified by silica gel chromatography (50% ethyl acetate in hexane, Rf=0.15) to afford the title compound. MS (APCI) m/z=362 (M+H)+.

Provenance & Evidence