Methanol → (1R,2R)-2-(4-aminophenyl)cyclopropane-1-carboxylic acid

Participants

Reaction Steps

To a 25 mL RB flask fitted with magnetic stirrer was charged 5 mL of methanol: and 5 mL of THF. To the stirred solvent, was added methyl (1R,2R)-2-(4-aminophenyl)cyclo propane carboxylate (1 g, 5.23 mmol) and NaOH (0.627 g, 15.69 mmol) in water (3 mL). The resulting solution was stirred at RT for 3 h. After completion of the reaction (reaction monitored by TLC), solvent was removed under reduced pressure. The RM was diluted with 3 mL of water, cooled to 0° C., then acidified to pH 3 with 1N HCl, and extracted with ethyl acetate (50 mL×2). The organic layer was washed water (50 mL), and saturated brine solution (30 mL). The organic layer was dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. The product was obtained as white color solid (0.9 g, yield: 97.2%).

Provenance & Evidence