反応 #44639

反応方程式

sodium hydrogensulfite

sodium hydroxide

hydrogen peroxide

lithium tri-sec-butyl borohydride

(S)-4-[(1R,2R)-2-tert-butyldiphenylsilanyloxy-1-(3,4,5-trifluorophenyl)propyl]-6-methylmorpholin-2,3-dione

→

title compound

収率 97.5%

(S)-4-[(1R,2R)-2-tert-butyl-diphenylsilanyloxy-1-(3,4,5-trifluorophenyl)propyl]-2-hydroxy-6-methylmorpholin-3-one

収率 97.5%

溶媒

ethyl acetate

THF

THF

反応条件

後処理

1. 1
   その他The resulting reaction solution
2. 2
   その他The resulting reaction solution
3. 3
   workup.STIRRINGwas stirred under ice-
4. 4
   温度cooling for 1 hr
5. 5
   その他The resulting reaction solution
6. 6
   workup.STIRRINGwas stirred at room temperature for 30 min
7. 7
   その他The organic layer was separated
8. 8
   洗浄washed with saturated saline
9. 9
   乾燥dried over anhydrous magnesium sulfate
10. 10
    濃縮concentrated under reduced pressure
11. 11
    その他The residue was purified by silica gel column chromatography (heptane:ethyl acetate=1:1)

実験手順

In nitrogen atmosphere, a THF solution (0.25 mL) of 1.06 M lithium tri-sec-butyl borohydride was dropwise added at −20° C. to a THF solution (3 mL) of (S)-4-[(1R,2R)-2-tert-butyldiphenylsilanyloxy-1-(3,4,5-trifluorophenyl)propyl]-6-methylmorpholin-2,3-dione (95 mg). The resulting reaction solution was stirred at −20° C. for 30 min. To the reaction solution, a 5 N sodium hydroxide aqueous solution (0.03 mL) and a 30% hydrogen peroxide aqueous solution (0.07 mL) were added in this order. The resulting reaction solution was stirred under ice-cooling for 1 hr, and a sodium hydrogensulfite powder (20 mg) was added thereto. The resulting reaction solution was stirred at room temperature for 30 min, and then saturated saline and ethyl acetate were added thereto. The organic layer was separated, washed with saturated saline, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (heptane:ethyl acetate=1:1) to give 93 mg of the title compound. The physical property values of this compound were as follows:

出典