[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]1[CH2:11][CH2:10][CH2:9][C:8]1=[O:12].C(O)C.[Na].C(O)(=O)C>C(Cl)Cl.O>[OH:12][CH:8]1[CH2:9][CH2:10][CH2:11][CH:7]1[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1In an argon gas stream atmosphere, 80.0 g (496 mM) of 2-(2-pyridyl)cyclopentanone and 1600 ml of dry ethanol were placed in a 2 liter-three-necked flask, followed by stirring at room temperature and then addition thereto of 18.7 g (496 mM) of sodium boronhydride. The system was then stirred for 2 hours at room temperature, followed by addition thereto of a small amount of acetic acid and water. The reaction mixture was methylene chloride. The organic layer was dried with anhydrous sodium sulfate and subjected to distilling-off of the solvent under reduced pressure to obtain a residue. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=3/1) to obtain 61.0 g of 1-hydroxy-2-(2-pyridyl)cyclopentane (Yield: 75.3%)
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