Reactive compound

Synthesis of Compound 3

[0155]

[0156]Into a four-necked flask were added 9.50 g (20.00 mmol) of a compound 1 synthesized by a method described in International Publication (WO2011 / 052709A1) and 100 mL of diethyl ether, and an argon gas was introduced into and bubbled through the resultant reaction liquid at room temperature (25° C.) for 30 minutes. The reaction liquid was cooled down to −70° C., then, 29.3 mL of a -butyllithium solution (1.64 mol / L, hexane solution) was added, and the mixture was stirred at room temperature for 2 hours. The reaction liquid was cooled down to −70° C., then, 5.20 g (50.00 mmol) of trimethoxyborane was added, and the mixture was stirred for 2 hours at −70° C. with no variation of temperature. Disappearance of a peak of the compound 1 and generation of a compound 2 were confirmed by liquid chromatography, and the reaction was terminated.

[0157]Into the reaction liquid was charged a 10 w % acetic acid aqueous solution (100 mL), and a liquid separating oper

Synthesis of Compound 6

[0160]

[0161]Into a four-necked flask were added 10.62 g (20.00 mmol) of a compound 4 synthesized by a method described in International Publication (WO2011 / 052709A1) and 100 mL of diethyl ether, and an argon gas was introduced into and bubbled through the resultant reaction liquid at room temperature (25° C.) for 30 minutes. The reaction liquid was cooled down to −70° C., then, 29.3 mL of a -butyllithium solution (1.64 mol / L, hexane solution) was added, and the mixture was stirred at room temperature for 2 hours. The reaction liquid was cooled down to −70° C., then, 5.20 g (50.00 mmol) of trimethoxyborane was added, and the mixture was stirred for 2 hours at −70° C. with no variation of temperature. Disappearance of a peak of the compound 4 and generation of a compound 5 were confirmed by liquid chromatography, and the reaction was terminated.

[0162]Into the reaction liquid was charged a 10 w % acetic acid aqueous solution (100 mL), and a liquid separating ope

Synthesis of Compound 9

[0165]

[0166]Into a four-necked flask were added 2.91 g (4.00 mmol) of a compound 7 synthesized by a method described in International Publication (WO2011 / 052709A1) and 20 mL of diethyl ether, an argon gas was introduced into and bubbled through the resultant reaction liquid at room temperature (25° C.) for 30 minutes. The reaction liquid was cooled down to −70° C., then, 5.9 mL of a -butyllithium solution (1.64 mol / L, hexane solution) was added, and the mixture was stirred at room temperature for 2 hours. The reaction liquid was cooled down to −70° C., then, 1.04 g (10.00 mmol) of trimethoxyborane was added, and the mixture was stirred for 2 hours at −70° C. with not variation of temperature. Disappearance of a peak of the compound 7 and generation of a compound 8 were confirmed by liquid chromatography, and the reaction was terminated.

[0167]Into the reaction liquid was charged a 10 w % acetic acid aqueous solution (20 mL), and a liquid separating operation w