Reaktion #44639

Reaktionsgleichung

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

Ausbeute 97.5%

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

Ausbeute 97.5%

Lösungsmittel

ethyl acetate

THF

THF

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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:

Quelle