Реакция #44639

Уравнение реакции

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

Выход 97.5%

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

Выход 97.5%

Растворители

ethyl acetate

THF

THF

Условия реакции

Обработка

1. 1
   ДругоеThe resulting reaction solution
2. 2
   ДругоеThe resulting reaction solution
3. 3
   workup.STIRRINGwas stirred under ice-
4. 4
   Температураcooling for 1 hr
5. 5
   ДругоеThe resulting reaction solution
6. 6
   workup.STIRRINGwas stirred at room temperature for 30 min
7. 7
   ДругоеThe organic layer was separated
8. 8
   Промывкаwashed with saturated saline
9. 9
   Сушкаdried over anhydrous magnesium sulfate
10. 10
    Концентрированиеconcentrated under reduced pressure
11. 11
    ДругоеThe residue was purified by silica gel column chromatography (heptane:ethyl acetate=1:1)

Методика

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:

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