反应详情

Under an argon atmosphere, a solution of cerium chloride (8.66 g, 3.0 equivalents) in THF (80 mL) was stirred at room temperature (25° C.) for 30 min. Sodium borohydride (1.37 g, 3.1 equivalents) was added, and the mixture was stirred at room temperature for 1 hr. Then bis(2-methylphenyl)phosphine oxide (2.7 g, 11.72 mmoL) synthesized in Reference Example 9 and lithium aluminum hydride (0.53 g, 1.2 equivalents) were successively added at 5° C., and the mixture was stirred at room temperature for 4 hrs. Toluene (80 mL) was added at 3° C., and then 3M-HCl (30 mL) was added. The mixture was stirred at room temperature for 30 min. The reaction mixture was partitioned, and the aqueous layer was extracted with toluene (20 mL). The combined organic layer was washed with 5% aqueous NaCl solution (20 mL). The organic layer was dried over anhydrous magnesium sulfate, filtered by gravity, and the filtrate was concentrated under reduced pressure. Toluene (20 mL) and silica gel (10 g) were added to the residue and the mixture was stirred at room temperature for 10 min. The mixture was filtered by gravity, and the filtrate was concentrated under reduced pressure. THF (5 mL) and BH3.THF (5 mL) were added to the residue at 5° C., and the mixture was stirred at room temperature for 1 hr. The mixture was concentrated under reduced pressure and the residue was recrystallized from heptane to give the title compound (1.15 g, white crystals). yield 43.0%. melting point: 78.0° C.

1. additionwere successively added at 5° C.
2. stirringthe mixture was stirred at room temperature for 4 hrs
3. stirringThe mixture was stirred at room temperature for 30 min
4. customThe reaction mixture was partitioned
5. extractionthe aqueous layer was extracted with toluene (20 mL)
6. washThe combined organic layer was washed with 5% aqueous NaCl solution (20 mL)
7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
8. filtrationfiltered by gravity
9. concentrationthe filtrate was concentrated under reduced pressure
10. additionToluene (20 mL) and silica gel (10 g) were added to the residue
11. stirringthe mixture was stirred at room temperature for 10 min
12. filtrationThe mixture was filtered by gravity
13. concentrationthe filtrate was concentrated under reduced pressure
14. additionTHF (5 mL) and BH3.THF (5 mL) were added to the residue at 5° C.
15. stirringthe mixture was stirred at room temperature for 1 hr
16. concentrationThe mixture was concentrated under reduced pressure
17. customthe residue was recrystallized from heptane