Methanol → [1-(3,5-Dimethoxyphenyl)pyrrolidin-2-yl]acetic acid

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Reaction Steps

A mixture of 53.6 g. (0.192 mole) methyl dl-2-[1-(3,5-dimethoxyphenyl)pyrrolidin-2-yl]acetate and 250 ml. methanol was warmed to obtain a solution and 22.8 g. (0.57 mole) sodium hydroxide in 200 ml. water was added. The resulting mixture was stirred at room temperature for 2.5 hours, the methanol evaporated and the aqueous residue cooled in ice. To this was added dropwise 48 ml. concentrated hydrochloric acid, the mixture extracted with 4x 150 ml. methylene chloride, the extract washed with water, dried (MgSO4) and the solvent evaporated to afford 48.9 g. (96%) of product. 1H-NMR (CDCl3) ppm (delta): 3.80 (s, 6H, OCH3), 4.10 (m, 1H, N--CH), 5.82 (s, 3H, aromatic), 11.0 (s, 1H, COOH). Mass spectrum (m/e): 206 (base peak), 265 (m+).

Provenance & Evidence