Hydrochloric Acid → 4-(1-(Benzyloxycarbonyl)pyrrolidin-2-yl)-2-fluorobenzoic acid

Participants

Reaction Steps

To a solution of benzyl 2-(3-fluoro-4-(methoxycarbonyl)phenyl)pyrrolidine-1-carboxylate (8.7 g, 24.4 mmol) in tetrahydrofuran (90 mL) was added lithium hydroxide monohydrate (2.05 g, 48.8 mmol) in 90 mL of water (90 mL) and methanol (90 mL) was added until a transparent solution formed. This mixture was stirred at ambient temperature for 2 hours and acidified with 2N hydrochloric acid to pH=2. The mixture was concentrated to about 90 mL, diluted with water and left to stand at ambient temperature overnight. The solid was collected by filtration, washed with water and dried to give 4-(1-(benzyloxycarbonyl)pyrrolidin-2-yl)-2-fluorobenzoic acid (8.4 g, yield 98%). LC-MS (ESI) m/z: 344 (M+1)+.

Provenance & Evidence