[F:1][C:2]1[C:7]([C:8]2[CH2:12][CH2:11][CH:10]([OH:13])[CH:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1>O1CCCC1.[Pd]>[F:1][C:2]1[C:7]([CH:8]2[CH2:12][CH2:11][CH:10]([OH:13])[CH2:9]2)=[CH:6][CH:5]=[CH:4][N:3]=1A solution of 3-(2-fluoropyridin-3-yl)cyclopent-2-enol (1184 mg, 6.61 mmol) in tetrahydrofuran (40 mL) was treated with palladium, 10% wt. on activated carbon (703 mg, 0.661 mmol). The reaction mixture was evacuated under vacuum and backfilled with hydrogen (3×), and stirred under hydrogen at 23° C. After 4 h, the reaction was filtered through celite, the filter cake washed with 1:1 methanol:dichloromethane (50 mL), the filtrates combined and concentrated, affording the product as a yellow oil. MS (ESI, pos. ion) m/z: 182.0 (M+1).
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