Reacción #44611

Ecuación de reacción

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

Rendimiento 97.5%

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

Rendimiento 97.5%

Disolventes

ethyl acetate

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGThis reaction solution was stirred under ice-
2. 2
   Temperaturacooling for 1 hr
3. 3
   workup.STIRRINGthis reaction solution was stirred at room temperature for 30 min
4. 4
   OtroThe organic layer was separated
5. 5
   Lavadowashed with saturated saline
6. 6
   Secadodried over anhydrous magnesium sulfate
7. 7
   Concentraciónconcentrated under reduced pressure
8. 8
   OtroThe obtained residue was purified by silica gel column chromatography (eluting solvent; heptane ethyl acetate=1:1)

Procedimiento

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:

Fuente