Trifluoroacetic acid → (2S)-2-(3-fluoro-4-methylbenzyl)pyrrolidine
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[CH3:21])[CH2:5][C@@H:6]1[CH2:10][CH2:9][CH2:8][N:7]1C(OC(C)(C)C)=O.FC(F)(F)C(O)=O>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[CH3:21])[CH2:5][C@@H:6]1[CH2:10][CH2:9][CH2:8][NH:7]1Participants
4
Procedure
A solution of tert-butyl (2S)-2-(3-fluoro-4-methylbenzyl)pyrrolidine-1-carboxylate (0.95 g, 3.24 mmol), which had been obtained in Example 1 (1d), in methylene chloride (9 mL) was added with trifluoroacetic acid (2.40 mL, 32.3 mmol), and stirred at room temperature for 2 hours. The reaction solution was concentrated under reduced pressure. The residue was added with saturated aqueous sodium hydrogen carbonate solution (20 mL) and extracted with methylene chloride (20 mL×3). After that, the organic layers were dried over sodium sulfate. The solvent was distilled off under reduced pressure to give the title compound as a yellow oily substance (0.44 g, yield 71%).