Reaction #44610

Reaction equation

oxalyl chloride

methylene chloride

(S)-1-[(1R,2R)-2-tert-butyldiphenylsilanyloxy-1-(3,4,5-trifluorophenyl)propylamino]propan-2-ol

water

→

title compound

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

Solvents

ethyl acetate

Conditions

Workup

1. 1
   Temperaturecooling
2. 2
   Temperaturecooling for 2 hr
3. 3
   OtherThe organic layer was separated
4. 4
   Washwashed with water, 1 N hydrochloric acid, water
5. 5
   DryingThen, the organic layer was dried over anhydrous magnesium sulfate
6. 6
   Concentrationconcentrated under reduced pressure
7. 7
   OtherThe residue was purified by silica gel column chromatography (eluting solvent; heptane:ethyl acetate=9:1 to 3:1)

Procedure

In nitrogen atmosphere, oxalyl chloride (45 μL) was dropwise added to a methylene chloride solution (2 mL) of (S)-1-[(1R,2R)-2-tert-butyldiphenylsilanyloxy-1-(3,4,5-trifluorophenyl)propylamino]propan-2-ol (171 mg), TEA (0.17 mL), and 4-(N,N-dimethylamino)pyridine (8 mg) under ice-cooling. This reaction solution was stirred under ice-cooling for 2 hr. To the reaction solution, iced-water and ethyl acetate were added. The organic layer was separated, washed with water, 1 N hydrochloric acid, water, a saturated sodium hydrogencarbonate aqueous solution, and saturated saline in this order. Then, the organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent; heptane:ethyl acetate=9:1 to 3:1) to give 96 mg of the title compound. The physical property values of this compound were as follows:

Source