(2R,5S)-2-(Acetylamino-methyl)-5-(3-trifluoromethoxy-phenylcarbamoyl)-pyrrolidine-1-carboxylic acid benzyl ester → (2S,5R)-5-(Acetylamino-methyl)-pyrrolidine-2-carboxylic acid (3-trifluoromethoxy-phenyl)-amide
Reaction equation
C(OC([N:11]1[C@H:15]([C:16](=[O:29])[NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([O:24][C:25]([F:28])([F:27])[F:26])[CH:19]=2)[CH2:14][CH2:13][C@@H:12]1[CH2:30][NH:31][C:32](=[O:34])[CH3:33])=O)C1C=CC=CC=1>C1COCC1.[Pd]>[F:27][C:25]([F:26])([F:28])[O:24][C:20]1[CH:19]=[C:18]([NH:17][C:16]([C@@H:15]2[CH2:14][CH2:13][C@H:12]([CH2:30][NH:31][C:32](=[O:34])[CH3:33])[NH:11]2)=[O:29])[CH:23]=[CH:22][CH:21]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of (2R,5S)-2-(acetylamino-methyl)-5-(3-trifluoromethoxy-phenylcarbamoyl)-pyrrolidine-1-carboxylic acid benzyl ester (48 mg, 0.1 mmol) in THF (0.3 mL) was added Pd/C (10%, 2.1 mg). The solution was degassed 3 times replacing air by nitrogen and finally nitrogen by hydrogen. The reaction mixture was further stirred under hydrogen atmosphere for 5 h. The catalyst was removed through a pad of Celite and washed with THF. Solvents were concentrated and the resulting residue was used without further purification in the next step. MS (LC/MS): 346 [M+H]+; tR (HPLC conditions b): 2.94 min.