benzyl (3R,5S)-1-(2-(1H-imidazol-5-yl)acetyl)-5-(4-(4-fluorophenoxy)phenylcarbamoyl)pyrrolidin-3-ylcarbamate → (2S,4R)-1-(2-(1H-imidazol-5-yl)acetyl)-4-amino-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide

Participants

Reaction Steps

A flask was charged with benzyl (3R,5S)-1-(2-(1H-imidazol-5-yl)acetyl)-5-(4-(4-fluorophenoxy)phenylcarbamoyl)pyrrolidin-3-ylcarbamate (800 mg, 1.43 mmol), prepared as in Example 1, palladium on carbon (10%, 80 mg) and methanol (30 mL) and the mixture was placed under a hydrogen atmosphere at 40 psi (parr shaker). The reaction was allowed to proceed for 4 hours and the mixture was filtered and concentrated. Product was purified from the residue by reverse phase HPLC to give (2S,4R)-1-(2-(1H-imidazol-5-yl)acetyl)-4-amino-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide (516 mg, 1.22 mmol, 85%) as an off-white solid.

Provenance & Evidence