Dimethylformamide → HCID 131726835, compound

Participants

Reaction Conditions

Reaction Steps

2-(R)-{2-[5-Iodo-2-(2-methoxyethoxy)phenyl]-1-(R)-methyoxycarbonylethyl}pyrrolidine-1-carboxylic acid tert-butyl ester (0.25 g, 0.44 mmol) is dissolved in DMF (5 mL), degassed, and treated with tetrakis(triphenylphosphine) palladium zero (0.05 g, 0.044 mmol) and zinc cyanide (0.156 g, 1.33 mmol) under nitrogen. The reaction mixture is warmed to 73° C. for 2.5 h, cooled and diluted with ethyl acetate (100 mL). The resulting precipitate is removed and the filtrate is washed with water and brine and dried over MgSO4. The solvent is removed in vacuo and the residue is subjected to flash chromatography (ethyl acetate/hexane/methylene chloride: 1/2/1). The title compound is isolated a syrup (0.15 g, mmol). 1H NMR (CDCl3, 300 MHz) □ 7.50-7.38(m, 2H), 7.15(d, 1H), 5.31(s, 2H), 4.23-4.11(m, 1H), 3.83-3.76(m, 2H), 3.57(s, 3H), 3.56-3.48(m, 2H), 3.37(s, 3H), 3.36-3.26(m, 3H), 2.94-2.78(m, 1H), 2.76-2.61(m, 1H), 2.03-1.75(m, 4H), 1.45(s, 9H).

Provenance & Evidence