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0 °C

740 mg of (R)-tert-butyl 1-hydroxypropan-2-ylcarbamate was dissolved in 30 mL of tetrahydrofuran in a nitrogen atmosphere, and 1.44 g of N-(2-chlorophenethyl)-2-nitrobenzenesulfonamide and 3.3 g of triphenylphosphine were added thereto. 2.5 mL of diisopropyl azodicarboxylate was added thereto at 0° C., and the mixture was stirred at room temperature for 4 hours. The reaction solution was concentrated under reduced pressure, and the obtained residue (intermediate) was dissolved in 20 mL of dichloromethane. To the solution, 2 mL of trifluoroacetic acid was added, and the mixture was stirred at room temperature for 6 hours. The reaction solution was neutralized with a saturated aqueous solution of sodium bicarbonate, followed by extraction with dichloromethane (30 mL×3). The organic layer was dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The obtained crude product was purified by silica gel column chromatography (dichloromethane:methanol=10:1) to obtain 380 mg of the title compound as a pale yellow oil (23%).

1. additionwere added
2. concentrationThe reaction solution was concentrated under reduced pressure
3. dissolutionthe obtained residue (intermediate) was dissolved in 20 mL of dichloromethane
4. additionTo the solution, 2 mL of trifluoroacetic acid was added
5. stirringthe mixture was stirred at room temperature for 6 hours
6. extractionfollowed by extraction with dichloromethane (30 mL×3)
7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
8. filtrationAfter filtration
9. concentrationthe filtrate was concentrated under reduced pressure
10. customThe obtained crude product
11. customwas purified by silica gel column chromatography (dichloromethane:methanol=10:1)