Reaktion #429206

Reaktionsgleichung

5-bromoindole

t-butylmagnesium chloride

ethyl acetate

sodium bicarbonate

→

solid

Ausbeute 72.0%

(R)-3-(N-Benzyloxycarbonylpyrrolidin-2-ylcarbonyl)-5-bromo-1H-indole

Ausbeute 72.0%

Lösungsmittel

diethyl ether

diethyl ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe organic layer was dried
2. 2
   Sonstigeevaporated under reduced pressure
3. 3
   Sonstigeto provide a yellow oil
4. 4
   SonstigeThe title compound was crystallized

Vorschrift

N-Benzyloxycarbonyl-R-proline acid chloride from the above reaction was dissolved in anhydrous diethyl ether (30 mL) and added at 0° C. to a solution of 5-bromoindole (2.9 g, 15.0 mmol) and t-butylmagnesium chloride (2M solution in diethyl ether, 8.3 mL, 16.5 mmol) in anhydrous diethyl ether (30 mL). The resulting mixture was stirred at room temperature under argon for 45 minutes and then ethyl acetate (150 mL) and saturated sodium bicarbonate (30 mL) were added. The organic layer was dried and evaporated under reduced pressure to provide a yellow oil. The title compound was crystallized using hexane/ethyl acetate (9:1) to provide a white solid (3.07 g, 72%). mp 95°-96° C.

Quelle