Reaktion #44625

Reaktionsgleichung

ammonium chloride

(S)-3-benzyloxymethyl-5-oxomorpholine-4-carboxylic acid tert-butyl ester

1-Bromo-3,4,5-trifluorobenzene

magnesium

→

title compound

{(S)-1-benzyloxymethyl-2-[2-oxo-2-(3,4,5-trifluorophenyl)ethoxy]ethyl}carbamic acid tert-butyl ester

Lösungsmittel

tetrahydrofuran

diethylether

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe resulting reaction solution
2. 2
   SonstigeThe resulting reaction solution
3. 3
   workup.STIRRINGwas stirred at −40° C. for 1 hr
4. 4
   Sonstigeat −40° C
5. 5
   SonstigeThe resulting reaction solution
6. 6
   Temperaturwas warmed up to room temperature
7. 7
   SonstigeThe organic layer was separated
8. 8
   Waschenwashed with saturated saline
9. 9
   Trocknendried over anhydrous magnesium sulfate
10. 10
    Einengenconcentrated under reduced pressure
11. 11
    SonstigeThe residue was purified by silica gel column chromatography (heptane-ethyl acetate system)

Vorschrift

1-Bromo-3,4,5-trifluorobenzene (446 μL) was dropwise added to a diethylether suspension (5 mL) of magnesium (249 mg) over 10 min at 40° C. The resulting reaction solution was stirred at 40° C. for 1 hr and then dropwise added to a tetrahydrofuran solution (30 mL) of (S)-3-benzyloxymethyl-5-oxomorpholine-4-carboxylic acid tert-butyl ester (1.1 g) over 10 min at −40° C. The resulting reaction solution was stirred at −40° C. for 1 hr, and a saturated ammonium chloride aqueous solution was gradually added dropwise thereto at −40° C. The resulting reaction solution was warmed up to room temperature, and then ethyl acetate was added thereto. The organic layer was separated, washed with saturated saline, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (heptane-ethyl acetate system) to give 952 mg of the title compound. The physical property values of this compound were as follows:

Quelle