Reaction #417947

Reaction equation

benzyl chloroformate

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

THF

NaHCO3

→

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

Solvents

H2O

Conditions

Workup

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

Procedure

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).

Source