C([N:8]1[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]([CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[C:19]([CH3:24])[CH:18]=2)[CH2:9]1)C1C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[F:23][C:20]1[CH:21]=[CH:22][C:17]([O:16][CH2:15][CH:10]2[CH2:11][CH2:12][CH2:13][CH2:14][NH:8][CH2:9]2)=[CH:18][C:19]=1[CH3:24]A solution of 1-5 (226 mg, 0.690 mmol) in MeOH (5 ml) was treated with 10 mol % palladium hydroxide on carbon (48.5 mg, 0.069 mmol). The flask was evacuated and backfilled with H2(g) three times and stirred under a H2(g) atmosphere (1 atm) at RT for 30 min. The mixture was filtered though a syringe filter and the filtrate was concentrated to yield 1-6. Data for 1-6: LRMS m/z (M+H): 238.1.
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