Reacción #5702

Ecuación de reacción

ethyl chloroformate

ethyl α-[3(trifluoromethyl)-benzylamino]-indole-3-acetate

sodium hydride

→

title compound

Rendimiento 66.4%

Ethyl α-[3(trifluoromethyl)-benzylamino]-1-ethoxycarbonyl-indole-3-acetate hydrochloride

Rendimiento 66.4%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGStirring
2. 2
   workup.WAITwas continued for two hours at room temperature
3. 3
   OtroAt the end of this time, the reaction contents
4. 4
   Extracciónthe aqueous solution extracted with ether
5. 5
   Lavadothe ether solution washed with saturated brine
6. 6
   Secadodried over anhydrous Na2SO4
7. 7
   OtroRemoval of the solvent in vacuo
8. 8
   Otrogave the crude product which
9. 9
   Otrowas chromatographed with 80 g of silica gel

Procedimiento

To a magnetically stirred solution of ethyl α-[3(trifluoromethyl)-benzylamino]-indole-3-acetate (1.00 g, 2.66 mmol) in 15 mL of DMF was added under nitrogen 0.112 g (2.79 mmol) of sodium hydride (60% oil dispersion). After stirring at room temperature for 10 minutes, 0.26 ml (2.79 mmol) of ethyl chloroformate was added. Stirring was continued for two hours at room temperature. At the end of this time, the reaction contents were poured into ice water, the aqueous solution extracted with ether and the ether solution washed with saturated brine and dried over anhydrous Na2SO4. Removal of the solvent in vacuo gave the crude product which was chromatographed with 80 g of silica gel using hexane-ethyl acetate (4:1) to yield 0.857 g of the title compound.

Fuente