N,N-Dimethylglycine → HCID 57864746, compound

Participants

Reaction Steps

A mixture of racemic trans-2-(1-benzyl-4-(2-bromophenyl)pyrrolidin-3-yl)-4-chlorophenol (1.8 g, 4.07 mmol), cesium carbonate (2.65 g, 8.13 mmol, 2.0 eq.), N,N-dimethylglycine (165 mg, 1.6 mmol; 0.4 eq.) and CuI (310 mg, 1.6 mmol; 0.4 eq.) in dioxane (20 ml) was heated to reflux temperature while stirring under inert nitrogen atmosphere. After one hour the title product was formed according to mass analysis (M+1=362, 364 found), but the conversion was not yet complete. Heating was continued overnight to give 98% conversion according to LC-MS. 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 the title compound (1.47 g, 4.06 mmol) in quantitative yield as a brown oil, with ca. 78% purity according to LC-MS analysis. The product was used without further purification. MS: M+1=362, 364 found.

Provenance & Evidence