Reaktion #40607

Reaktionsgleichung

5-aminoindane

ethyl 3-chloropropionate

potassium carbonate

→

title compound

Ausbeute 71.0%

3-(Indan-5-ylamino)-propionic acid ethyl ester

Ausbeute 71.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling to room temperature (rt)
2. 2
   Extraktionthe mixture was extracted into ethyl acetate (EtOAc)
3. 3
   Waschenwashed with water, brine
4. 4
   Trocknendried with sodium sulfate (Na2SO4)
5. 5
   SonstigeRemoval of the solvent and chromatography on silica
6. 6
   Wascheneluting with EtOAc/hexanes (1:20-1:10

Vorschrift

To a mixture of 5-aminoindane (5 g, 37.6 mmol), ethyl 3-chloropropionate (4.7 mL, 37.6 mmol) and potassium carbonate (5.2 g, 37.6 mmol) was added tetrabutylammonium bromide (200 mg). The mixture was stirred at 100° C. for 16 hours. After cooling to room temperature (rt), the mixture was extracted into ethyl acetate (EtOAc), washed with water, brine and then dried with sodium sulfate (Na2SO4). Removal of the solvent and chromatography on silica, eluting with EtOAc/hexanes (1:20-1:10, v/v), gave 6.2 g (71%) of the title compound. 1H NMR (300 MHz, CDCl3) δ (ppm): 7.03 (d, J=7.6 Hz, 1H), 6.55 (s, 1H), 6.43 (d, J=7.6 Hz, 1H), 4.15 (q, 2H), 3.86 (br, 1H), 3.43 (t, 2H), 2.82 (m, 4H), 2.60 (t, 2H), 2.06 (m, 2H), 1.27 (t, 3H).

Quelle