Potassium Phosphate, Tribasic → (R)-[4'-(1-{4-[3-(t-butyl-dimethyl-silanyloxy)-4,4-dimethyl-pentyl]-3-methyl-phenyl}-1-ethyl-propyl)-2'-methyl-biphenyl-3-yl]-hydroxy-acetic Acid Methyl Ester

Participants

Reaction Steps

Degassed toluene (0.17 mL) was added to t-butyl-(1-{2-[4-(1-ethyl-1-{4-[4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl]-3-methyl-phenyl}-propyl)-2-methyl-phenyl]-ethyl}-2,2-dimethyl-propoxy)dimethylsilane (Example 23-(1); 46.5 mg, 0.0766 mmol), palladium (II) acetate (2.8 mg, 0.013 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl (10.5 mg, 0.0256 mmol) and potassium phosphate (39.8 mg, 0.187 mmol), and the mixture was stirred in a nitrogen atmosphere for three minutes. Then, a solution of (R)-(3-chloro-phenyl)hydroxy-acetic acid methyl ester (Example 156-(1); 18.8 mg, 0.0937 mmol) in toluene (0.17 mL) and water (0.033 mL) were added, and the mixture was heated while stirring at an external temperature of 95 to 105° C. for one hour. The reaction mixture was diluted with diethyl ether and filtered through cotton plug, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate=8/1) to give the title compound (35 mg, 71%).

Provenance & Evidence