N,N-Dimethylglycine → HCID 57864747, compound

Participants

Reaction Steps

A mixture of racemic trans-2-(1-(2,4-dimethoxybenzyl)-4-(2-bromophenyl)pyrrolidin-3-yl)-4-chlorophenol (6.8 g, 13.54 mmol), cesium carbonate (8.83 g, 27.1 mmol, 2.0 eq.), N,N-dimethylglycine (558 mg, 5.42 mmol; 0.4 eq.) and CuI (1.03 g, 5.42 mmol; 0.4 eq.) in dioxane (75 ml) was heated to reflux temperature overnight while stirring under inert nitrogen atmosphere to give 90% conversion according to LC-MS (M+1=422, 424 found). The reaction mixture was cooled to room temperature and was then filtered over a glass filter. The residual salts were washed with dioxane (25 ml). The combined filtrates were concentrated under vacuum to give the crude product as a brown oil. Toluene (150 ml) was added and the resulting solution was washed with concentrated aqueous ammonia (25 ml; 25%). The toluene layer was separated and dried with Na2SO4. Concentration under vacuum gave crude trans-5-chloro-2,3,3a,12b-tetrahydro-2-(2,4-dimethoxybenzyl)-1H-dibenz[2,3:6,7]-oxepino[4,5-c]pyrrole (6.2 g) in quantitative yield as a brown oil, with ca. 70% purity according to LC-MS analysis. The product was used without further purification.

Provenance & Evidence