Reaktion #44629

Reaktionsgleichung

iodine

triethyl phosphite

iodide

(4R,9aS)-4-(3,4,5-trifluorophenyl)hexahydropyrido[2,1-c][1,4]oxazin-6-one

N,N,N′,N′-tetramethylethylenediamine

sodium thiosulfate

→

title compound

[(4R,9aS)-6-oxo-4-(3,4,5-trifluorophenyl)octahydropyrido[2,1-c][1,4]oxazin-7-yl]phosphonic acid diethyl ester

Lösungsmittel

methylene chloride

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe resulting reaction solution
2. 2
   Temperaturcooling for 30 min
3. 3
   Temperaturunder ice-cooling
4. 4
   SonstigeThe resulting reaction solution
5. 5
   workup.STIRRINGwas stirred under ice-
6. 6
   Temperaturcooling for 1 hr
7. 7
   SonstigeThe organic layer was separated
8. 8
   Waschenwashed with saturated saline
9. 9
   Trocknendried over magnesium sulfate
10. 10
    Einengenconcentrated under reduced pressure
11. 11
    Sonstigeto give a crude
12. 12
    workup.ADDITIONwas added
13. 13
    workup.STIRRINGThe resulting mixture was stirred at 120° C. for 2 hr
14. 14
    Einengenconcentrated under reduced pressure

Vorschrift

In nitrogen atmosphere, trimethylsilyle iodide (0.188 mL) was added to a methylene chloride solution (6 mL) of (4R,9aS)-4-(3,4,5-trifluorophenyl)hexahydropyrido[2,1-c][1,4]oxazin-6-one (252 mg) and N,N,N′,N′-tetramethylethylenediamine (0.466 mL) at 0° C. The resulting reaction solution was stirred under ice-cooling for 30 min, and iodine (336 mg) was added thereto under ice-cooling. The resulting reaction solution was stirred under ice-cooling for 1 hr, and ethyl acetate and a saturated sodium thiosulfate aqueous solution were added thereto. The organic layer was separated, washed with saturated saline, dried over magnesium sulfate, and concentrated under reduced pressure to give a crude iodinated substance. To the given crude iodinated substance, triethyl phosphite (3 mL) was added. The resulting mixture was stirred at 120° C. for 2 hr, allowed to cool to room temperature, and then concentrated under reduced pressure to give 372 mg of the title compound. The physical property values of this compound were as follows:

Quelle