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0 °C

Lithium perchlorate (10.2 g) was added to a solution of (S)-1-(2-chloropyridin-4-yl)ethylamine obtained in Example 51 (1 g) in an ether (18.5 mL), and the reaction solution was stirred for five minutes. Isobutylene oxide (1.7 mL) was added to the reaction solution, which was then stirred overnight. A 5 N sodium hydroxide solution was added to the reaction solution at 0° C., followed by extraction with chloroform. The organic layer was dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. Dichloromethane (20 mL) and pyridine (20 mL) were added to the residue, and the reaction solution was cooled to 0° C. Oxalyl chloride (669 μL) was added to the reaction solution, which was then stirred at 0° C. for one hour and at room temperature for one hour. Oxalyl chloride (0.4 mL) was added to the reaction solution, which was further stirred for one hour. The solvent was evaporated under reduced pressure. Water and ethyl acetate were added to the residue, and the organic layer was separated. The organic layer was dried over magnesium sulfate, and the residue was purified by silica gel column chromatography (Chromatorex; elution solvent: heptane-ethyl acetate) to obtain the title compound (1.07 g). The property values of the compound are as follows.

1. stirringwas then stirred overnight
2. extractionfollowed by extraction with chloroform
3. dry with materialThe organic layer was dried over magnesium sulfate
4. customthe solvent was evaporated under reduced pressure
5. additionDichloromethane (20 mL) and pyridine (20 mL) were added to the residue
6. additionOxalyl chloride (669 μL) was added to the reaction solution, which
7. stirringwas then stirred at 0° C. for one hour and at room temperature for one hour
8. additionOxalyl chloride (0.4 mL) was added to the reaction solution, which
9. stirringwas further stirred for one hour
10. customThe solvent was evaporated under reduced pressure
11. additionWater and ethyl acetate were added to the residue
12. customthe organic layer was separated
13. dry with materialThe organic layer was dried over magnesium sulfate
14. customthe residue was purified by silica gel column chromatography (Chromatorex; elution solvent: heptane-ethyl acetate)