反应详情

A solution of cyclopentane methanol (4.05 ml, Ald) in anhydrous tetrahydrofuran (abbreviated as “THF” hereinafter, 40 ml) was added with triethylamine (6.49 ml, WAKO), added dropwise with methanesulfonyl chloride (3.48 ml, WAKO) under ice cooling, and stirred for 30 minutes. The reaction mixture was added with water (50 ml), and extracted with diethyl ether (80 ml×2). The organic layer was washed with saturated brine and dried, and then the solvent was evaporated under reduced pressure. A solution obtained beforehand by adding 60% sodium hydride (1.15 g, KANTO) to a solution of Intermediate 1 (4.50 g) in N,N-dimethylformamide (abbreviated as “DMF” hereinafter, 35 ml) under ice cooling and stirring the solution for 15 minutes was added with a solution of the aforementioned residue in DMF (10 ml) under ice cooling. The reaction mixture was stirred for 15 minutes, then warmed to room temperature, stirred for 45 minutes, and further stirred at 60° C. for 15 hours. The reaction mixture was added with water (100 ml) and diethyl ether (200 ml) for extraction. The organic layer was successively washed with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride, and saturated brine and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography (hexane:isopropyl ether=9:1) to obtain the title compound (Intermediate 2, 5.58 g).

1. extractionextracted with diethyl ether (80 ml×2)
2. washThe organic layer was washed with saturated brine
3. customdried
4. customthe solvent was evaporated under reduced pressure
5. customA solution obtained
6. stirring35 ml) under ice cooling and stirring the solution for 15 minutes
7. stirringThe reaction mixture was stirred for 15 minutes
8. stirringstirred for 45 minutes
9. stirringfurther stirred at 60° C. for 15 hours
10. washThe organic layer was successively washed with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride, and saturated brine
11. customdried
12. customthe solvent was evaporated under reduced pressure
13. customThe residue was purified by flash column chromatography (hexane:isopropyl ether=9:1)