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

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%).

1. customTo a 25 mL RB flask fitted with magnetic stirrer
2. customAfter completion of the reaction (reaction monitored by TLC), solvent
3. customwas removed under reduced pressure
4. additionThe RM was diluted with 3 mL of water
5. temperaturecooled to 0° C.
6. extractionextracted with ethyl acetate (50 mL×2)
7. washThe organic layer was washed water (50 mL), and saturated brine solution (30 mL)
8. dry with materialThe organic layer was dried over anhydrous Na2SO4
9. customthe solvent was removed under reduced pressure

ORD record

ord-4e0cd967895646a8b8319c0782d89f42

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09278915B2