Methanol → 3-[(3S)-1-Methyl-2-oxo-pyrrolidin-3-yl]oxy-5-phenylmethoxy-benzoic acid

Participants

Reaction Steps

Methyl 3-[(3S)-1-methyl-2-oxo-pyrrolidin-3-yl]oxy-5-phenylmethoxy-benzoate (Intermediate 9) (2.4 g, 6.8 mmol) was dissolved in THF (45 mL), methanol (15 mL) and 1 N lithiumhydroxide (8.1 mL). Water (60 mL) was added dropwise until the solution went cloudy and the resultant solution was stirred for 3 hours at room temperature. The organics were removed by evaporation under reduced pressure, the aqueous solution was filtered, acidified with 2N hydrochloric acid, extracted with ethyl acetate (3×20 mL), washed with water (10 mL), brine (10 mL) and evaporated to dryness under reduced pressure to give product (2.106 g, 92%). 1H NMR 6 (300 MHz, CDCl3) 2.07-2.21 (m, 1H), 2.51-2.65 (m, 1H), 2.96 (s, 3H), 3.32-3.55 (m, 2H), 4.92 (t, 1H), 5.06 (s, 2H), 6.88 (s, 1H), 7.28-7.46 (m, 7H); m/z 340 (M−H)−.

Provenance & Evidence