反応 #40607

反応方程式

5-aminoindane

ethyl 3-chloropropionate

potassium carbonate

→

title compound

収率 71.0%

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

収率 71.0%

反応条件

後処理

1. 1
   温度After cooling to room temperature (rt)
2. 2
   抽出the mixture was extracted into ethyl acetate (EtOAc)
3. 3
   洗浄washed with water, brine
4. 4
   乾燥dried with sodium sulfate (Na2SO4)
5. 5
   その他Removal of the solvent and chromatography on silica
6. 6
   洗浄eluting with EtOAc/hexanes (1:20-1:10

実験手順

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).

出典