Reaktion #5702

Reaktionsgleichung

ethyl chloroformate

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

sodium hydride

→

title compound

Ausbeute 66.4%

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

Ausbeute 66.4%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGStirring
2. 2
   workup.WAITwas continued for two hours at room temperature
3. 3
   SonstigeAt the end of this time, the reaction contents
4. 4
   Extraktionthe aqueous solution extracted with ether
5. 5
   Waschenthe ether solution washed with saturated brine
6. 6
   Trocknendried over anhydrous Na2SO4
7. 7
   SonstigeRemoval of the solvent in vacuo
8. 8
   Sonstigegave the crude product which
9. 9
   Sonstigewas chromatographed with 80 g of silica gel

Vorschrift

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.

Quelle