Reaktion #49965

Reaktionsgleichung

t-butyl bromoacetate

morpholine

→

morpholinoacetic acid

Ausbeute 85.0%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationfilter
2. 2
   Waschenwash the filter cake with ethyl ace tare
3. 3
   Waschenwash with saturated sodium bicarbonate (2×), water (2×) and brine
4. 4
   TrocknenDry (Na2SO4)
5. 5
   Filtrationfilter
6. 6
   Sonstigeevaporate the solvent in vacuo
7. 7
   Temperaturcool in ice
8. 8
   Sonstigebubble hydrogen chloride gas into the solution
9. 9
   workup.STIRRINGStir at room temperature overnight
10. 10
    Temperaturcool
11. 11
    Filtrationfilter

Vorschrift

Dissolve t-butyl bromoacetate (leq) in tetrahydrofuran and add morpholine (2.2 eq) via syringe. Stir the reaction mixture at room temperature for 2 hours, filter and wash the filter cake with ethyl ace tare. Combine the organic filtrates and wash with saturated sodium bicarbonate (2×), water (2×) and brine. Dry (Na2SO4), filter and evaporate the solvent in vacuo. Take up the oily residue in ethyl acetate, cool in ice and bubble hydrogen chloride gas into the solution. Stir at room temperature overnight, cool and filter to give morpholinoacetic acid (85%); mp 169°-170° C.; 1H NMR (D2O) δ3.75-4.29 (br m, 6), 3.59 (br s, 2), 3.28 (br s, 2).

Quelle