Reaktion #417947

Reaktionsgleichung

benzyl chloroformate

4-(1-amino-ethyl)-phenol hydrobromide

THF

NaHCO3

→

(S)-Benzyl 1-(4-hydroxyphenyl)ethylcarbamate

Lösungsmittel

H2O

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONare added
2. 2
   SonstigeAfterwards the reaction mixture is quenched by the addition of water
3. 3
   ExtraktionThen the product is extracted with EtOAc
4. 4
   Trocknenthe combined organic layers are dried over MgSO4
5. 5
   Filtrationfiltered
6. 6
   Sonstigethe solvent is removed in vacuo
7. 7
   SonstigeThe crude product is purified by flash chromatography (silica gel, PE/EtOAc)

Vorschrift

5.00 g (22.9 mmol) 4-(1-amino-ethyl)-phenol hydrobromide are added to 10 mL THF and 10 mL H2O before 13.5 g (160 mmol) NaHCO3 are added. Then 3.60 mL (25.2 mmol) benzyl chloroformate are added dropwise and the reaction mixture is stirred at r.t. for 3 h. Afterwards the reaction mixture is quenched by the addition of water and is set to a gentle acidic pH value using citric acid (10% in water). Then the product is extracted with EtOAc, the combined organic layers are dried over MgSO4, filtered and the solvent is removed in vacuo. The crude product is purified by flash chromatography (silica gel, PE/EtOAc).

Quelle