Reaction #44639

Reaction equation

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

Yield 97.5%

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

Yield 97.5%

Solvents

ethyl acetate

THF

THF

Conditions

Workup

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

Procedure

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:

Source