Реакция #44611

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-butyldiphenylsilanyloxy-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
   workup.STIRRINGThis reaction solution was stirred under ice-
2. 2
   Температураcooling for 1 hr
3. 3
   workup.STIRRINGthis reaction solution was stirred at room temperature for 30 min
4. 4
   ДругоеThe organic layer was separated
5. 5
   Промывкаwashed with saturated saline
6. 6
   Сушкаdried over anhydrous magnesium sulfate
7. 7
   Концентрированиеconcentrated under reduced pressure
8. 8
   ДругоеThe obtained residue was purified by silica gel column chromatography (eluting solvent; 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 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) at −20° C. This reaction solution was stirred at −20° C. for 30 min. To this reaction solution, a 5 N sodium hydroxide aqueous solution (0.03 mL) and a 30% hydrogen peroxide aqueous solution (0.07 mL) were added. This reaction solution was stirred under ice-cooling for 1 hr. A sodium hydrogensulfite powder (20 mg) was added to the reaction solution, and this reaction solution was stirred at room temperature for 30 min. To this reaction solution, saturated saline and ethyl acetate were added. The organic layer was separated, washed with saturated saline, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluting solvent; 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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