Acetic Acid → 3-(2-trifluoromethylphenyl)-7-((2S,3R)-2,3,4-trihydroxybutylamino)-2H-isoquinolin-1-one

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Reaction Steps

The 7-amino-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one (2.04 g, 0.986 mmol) obtained in step C of Example 1-1 and D-(−)-erythrose (807 mg, 6.72 mmol) were dissolved in methanol (40 ml). Thereafter, acetic acid (2.31 ml, 40.3 mmol) and a 1 M sodium cyanoborohydride THF solution (20.2 ml, 20.2 mmol) were added at 0° C. to the obtained solution, and the obtained mixture was then stirred at a room temperature for 4 hours. Thereafter, the reaction mixture was concentrated under reduced pressure, and water was then added to the concentrate, followed by extraction with methylene chloride. The extract was washed with a saturated saline solution, and was then dried over sodium sulfate, followed by concentration under reduced pressure. The obtained residue was purified by silica gel chromatography (methylene chloride:methanol=15:1 to 10:1), so as to obtain 3-(2-trifluoromethylphenyl)-7-((2S,3R)-2,3,4-trihydroxybutylamino)-2H-isoquinolin-1-one (1.15 g, 42%).

Provenance & Evidence