[F:1][C:2]1[C:7]([C:8]2[CH2:12][CH2:11][C:10](=[O:13])[CH:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[Cl-].[Ce+3].[Cl-].[Cl-].[B-].[Na+]>O1CCCC1.CO>[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]=1A solution of 3-(2-fluoropyridin-3-yl)cyclopent-2-enone (1582 mg, 8.93 mmol) in Tetrahydrofuran (20 mL) and Methanol (20 mL) was cooled to 0° C. under nitrogen. Cerium (III) chloride (2201 mg, 8.93 mmol) was added, followed by sodium borohydrate (676 mg, 17.86 mmol) in 4 lots, over 15 min. After 30 min, the reaction was quenched with saturated ammonium chloride solution (20 mL—effervescence!), and partitioned between dichloromethane (100 mL) and saturated ammonium chloride solution (30 mL). The organic layer was separated, and the aqueous layer was extracted with dichloromethane (50 mL). The organic layers were combined, dried over MgSO4, and concentrated, affording the product as a yellow oil. MS (ESI, pos. ion) m/z: 180.1 (M+1).
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