反応 #44611

反応方程式

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

収率 97.5%

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

収率 97.5%

溶媒

ethyl acetate

THF

THF

反応条件

後処理

1. 1
   workup.STIRRINGThis reaction solution was stirred under ice-
2. 2
   温度cooling for 1 hr
3. 3
   workup.STIRRINGthis reaction solution was stirred at room temperature for 30 min
4. 4
   その他The organic layer was separated
5. 5
   洗浄washed with saturated saline
6. 6
   乾燥dried over anhydrous magnesium sulfate
7. 7
   濃縮concentrated under reduced pressure
8. 8
   その他The obtained residue was purified by silica gel column chromatography (eluting solvent; heptane ethyl acetate=1:1)

実験手順

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:

出典