Hydrochloric Acid → 2-(3-(4-(4-Methoxybenzoyl)piperidin-1-yl)-2-oxopyrrolidin-1-yl)acetic acid

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Reaction Steps

To a solution of ethyl 2-(3-(4-(4-methoxybenzoyl)piperidin-1-yl)-2-oxopyrrolidin-1-yl)acetate (727 mg, 1.778 mmol) in ethanol (36 mL) was added a 2 N aqueous NaOH solution (1.8 mL). The mixture was stirred 1 hour at room temperature. The reaction was then neutralized to pH 7 with 1 N HCl. The solvents were removed in vacuo, then azeotroped 3 times with dichloromethane. The light yellow foamy solid was dried under high vacuum to afford the title racemic product (835 mg). MS (ESI) [m/e, (M+H)+]=360.9. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.89-8.01 (m, 2H), 6.96-7.11 (m, 2H), 3.85 (s, 3H), 3.46-3.68 (m, 2H), 3.13-3.46 (m, 5H), 2.93-3.04 (m, 1H), 2.61-2.84 (m, 1H), 2.30-2.42 (m, 1H), 1.95-2.11 (m, 1H), 1.81-1.95 (m, 1H), 1.64-1.78 (m, 2H), 1.44-1.63 (m, 2H).

Provenance & Evidence