Reaktion #44610

Reaktionsgleichung

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

Lösungsmittel

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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:

Quelle