3'-Hydroxyphenylacetic acid → HCID 68676419, compound

Participants

Reaction Steps

To a suspension of 3-hydroxy phenylacetic acid (1.52 g, 10.0 mmol) in 10 mL of DCM is added L-proline methyl ester hydrochloride (1.80 g, 10.0 mmol) followed by the addition of TEA (1.67 mL, 12 mmol), 1-hydroxybenzotriazole (HOBt, 1.17 g, 10 mmol), and EDCl (1.92 g, 10 mmol). The mixture is stirred at RT for 4 days. Ethyl acetate and water is added, and the organic layer is separated and washed with brine, dried over anhydrous sodium sulfate, and concentrated. The crude mixture is purified by flash chromatography (silica gel) eluting with hexane:ethyl acetate (1:2) to give (R)-1-[2-(3-hydroxy-phenyl)-acetyl]-pyrrolidine-2-carboxylic acid ethyl ester as an oil.

Provenance & Evidence