Reacción #53959

Ecuación de reacción

ammonium chloride

triethylamine

(S)-phenylglycinol

tert-butyl bromoacetate

→

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

Rendimiento 33.0%

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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%).

Fuente