Reaktion #53959

Reaktionsgleichung

ammonium chloride

triethylamine

(S)-phenylglycinol

tert-butyl bromoacetate

→

tert-butyl (S)-(2-Hydroxy-1-phenyl-ethylamino)-acetate

Ausbeute 33.0%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstirred for 15 h
2. 2
   Extraktionthe aqueous layer was extracted with diethyl ether (3 times)
3. 3
   WaschenThe combined extracts were washed with saturated sodium chloride solution
4. 4
   Trocknendried over magnesium sulfate
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated to dryness in vacuo
7. 7
   SonstigeThe resulting solid was recrystallized from a diethyl ether/n-hexane mixture

Vorschrift

Following the literature procedure (Panek, J., J. Org. Chem., 1998, 63, 2382), triethylamine (6.2 ml, 44.5 mmole) was added to a solution of (S)-phenylglycinol (5 g, 36.45 mmole) in anhydrous tetrahydrofuran (150 ml) under argon at 0° C. After stirring for 15 min, tert-butyl bromoacetate (5.9 ml, 39.96 mmole) was added slowly to this cooled solution. The resulting mixture was warmed to room temperature, and stirred for 15 h. Saturated ammonium chloride aqueous solution was added, and the aqueous layer was extracted with diethyl ether (3 times). The combined extracts were washed with saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated to dryness in vacuo. The resulting solid was recrystallized from a diethyl ether/n-hexane mixture to give tert-butyl (S)-(2-Hydroxy-1-phenyl-ethylamino)-acetate as a white solid (3 g, 33%).

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