N-tert-Butoxycarbonyl-(2R,4S)-4-fluoroproline benzyl ester → (2S,4S)-1-((tert-butoxy)carbonyl)-4-fluoropyrrolidine-2-carboxylic acid

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Reaction Steps

Methanol (95 mL) was carefully added to a mixture of 11 (2.8 g, 8.7 mmol) and palladium on carbon (10% w/w, 1.0 g, 0.94 mmol Pd) under Ar(g). A balloon filled with H2(g) was affixed to the reaction flask, and the mixture was stirred overnight. After 24 h, unreacted starting material remained, so an additional 0.95 g (0.89 mmol Pd) of Pd/C were added and a fresh balloon filled with H2(g) was placed on the flask. After stirring overnight, TLC indicated reaction had gone to completion, and the mixture was filtered through Celite. The filtrate was concentrated to a white solid by rotary evaporation under reduced pressure and dried under vacuum, affording 12 (1.8 g, 7.6 mmol, 87%), which was used without further purification.

Provenance & Evidence