[CH3:1][N:2]1[CH:6]=[C:5]([N+:7]([O-:9])=[O:8])[CH:4]=[C:3]1[CH:10]=[O:11].B.O1CCCC1>O1CCCC1>[OH:11][CH2:10][C:3]1[N:2]([CH3:1])[CH:6]=[C:5]([N+:7]([O-:9])=[O:8])[CH:4]=1Compound 22-1 (550 mg) was dissolved in anhydrous tetrahydrofuran (30 ml) and cooled to 0° C. To the solution was slowly added dropwise 1M borane-tetrahydrofuran (3.25 ml), followed by refluxing at 80° C. for 3 hours. After the completion of the reaction, the solvent was evaporated under reduced pressure to be removed, and then the residue was purified by column-chromatography (ethyl acetate/hexane=2/1) to yield the compound 22-2 (500 mg, 90%).
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