Sodium Chloride → HCID 57495615, compound

Participants

Reaction Conditions

Reaction Steps

In analogy to a procedure outlined in J. Chem. Soc. Perkin Trans. 1, 22, 1993, 2761-2772, methyl-α-bromophenylacetic acid (2.0 g) was dissolved in CH3CN and cooled to 0° C. by means of an ice bath. To this solution was added triethylamine (1.7 mL) dropwise and the mixture was stirred for 30 minutes. A solution of cyclopropylamine in CH3CN was then added dropwise at 0° C. over 5 minutes and stirring was continued for 2 hours. The mixture was poured into ice/water, saturated with NaCl and extracted with ethyl acetate. The organic layer was separated, washed with brine, dried over Na2SO4 and evaporated. The residue was purified by flash chromatography, eluting with a gradient of ethyl acetate in heptane (0 to 50% ethyl acetate). Fractions containing the product were combined and evaporated to give cyclopropylamino-phenyl-acetic acid methyl ester as a light yellow liquid (1.74 g). MS (ESI): 206.0 (MH+).

Provenance & Evidence