[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:19]#[N:20])([CH2:14][CH:15]([OH:18])CO)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].I([O-])(=O)(=O)=O.[Na+].O>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:19]#[N:20])([CH2:14][CH2:15][OH:18])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]To a solution of 4-cyano-4-(2,3-dihydroxypropyl)piperidine-1-carboxylic acid tert-butyl ester (3.65 g) in tetrahydrofuran (100 ml) was added 10% aqueous sodium periodate solution (100 ml), and the mixture was stirred at room temperature for 40 min. After completion of the reaction, water was added and the mixture was extracted with ethyl acetate and washed with saturated brine. The organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated. The obtained residue (3.3 g) was dissolved in tetrahydrofuran (100 ml) and sodium borohydride (360 mg) and methanol (20 ml) were added with ice-cooling, and the mixture was stirred at room temperature for 30 min. After completion of the reaction, 10% aqueous citric acid was added and the mixture was extracted with ethyl acetate and washed with saturated brine. The organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated. The obtained residue was purified by silica gel column chromatography (chloroform:methanol=95:5) and dried under reduced pressure to give the title compound (3.13 g).
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