[2-(4-HYDROXY-PHENYL)-ETHYL]-CARBAMIC ACID ETHYL ESTER synthesis

Yield:-

Reaction Conditions:

with sodium hydroxide in tetrahydrofuran;water at 20; for 18 h;

Steps:

1; 1.1

Add dropwise via an addition funnel a solution of ethyl chloroformate (0.74mL, 7. 7mmol) in tetrahydrofuran (7mL) to a stirred solution of tyramine (l. Og, 7. 3mmo : 1), sodium hydroxide (0.7g, 17. 1mmol), and water (7mL). Stir at room temperature for 18 hours then pour the reaction into 1N aqueous hydrochloric acid so the pH = 1-2. Extract with ethyl acetate (3x25mL). Dry the combined ethyl acetate extracts over sodium chloride/magnesium sulfate, filter, and concentrate on a rotary evaporator to yield 1. 3g, 6. 2mmol of [2- (4-hydroxy-phenyl)-ethyl]-carbamic acid ethyl ester :'H NMR (CDC13, 300.00 MHz): 7.01 (d, 2H); 6.78 (d, 2H); 6.26 (s, 1H) ; 4.78 (s, 1H); 4.14-4. 09 (m, 2H) ; 3.40-3. 38 (m, 2H); 2. 74-2. 69 (m, 2H); 1.24-1. 19 (m, 3H).

References:

WO2005/92836,2005,A1 Location in patent:Page/Page column 16; 31