C([O:8][CH2:9][C@@H:10]([C@H:20]1[CH2:24][CH2:23][NH:22][CH2:21]1)[O:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=1[CH3:19])C1C=CC=CC=1.C(O)(C(F)(F)F)=O.Cl>CCO.[OH-].[OH-].[Pd+2]>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([O:11][C@@H:10]([C@@H:20]2[CH2:24][CH2:23][NH:22][CH2:21]2)[CH2:9][OH:8])=[C:13]([CH3:19])[CH:14]=1To a solution of (S)-3-[(R)-2-benzyloxy-1-(4-chloro-2-methylphenoxy)ethyl]-pyrrolidine•TFA (4.6 mg, 10 μmol) in EtOH (2.0 mL) at room temperature, was added concentrated HCl (˜50 μL). To the stirred mixture was added 20% Pd(OH)2/C (50 wt % water, 4.0 mg). The resulting mixture was degassed and flushed with hydrogen three times and then hydrogenated under a hydrogen balloon for 25 minutes. The mixture was filtered and the filtrate was concentrated. The resulting residue was redissolved in a mixture of AcOH (0.5 mL) and water (1.0 mL), filtered and purified by reverse phase preparative HPLC to yield the title compound as a mono-TFA salt (0.6 mg, 98% purity). MS m/z: [M+H]+ calcd for C13H18ClNO2, 256.10; found 256.2.
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