Potassium Carbonate → 3-(Indan-5-ylamino)-propionic acid ethyl ester

HRID 12329

Reaktionsgleichung

Reaktionsgleichung von HRID 12329
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][CH2:6][CH2:5]2.Cl[CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].C(=O)([O-])[O-].[K+].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:17]([O:16][C:14](=[O:15])[CH2:13][CH2:12][NH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][CH2:6][CH2:5]2)[CH3:18]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 69341Ethyl 3-chloropropionateHCID 90496Indan-5-amine

Produkt 1

HCID 252228753-(Indan-5-ylamino)-propionic acid ethyl esterAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 74236Tetrabutylammonium BromideKatalysator

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

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).

Aufarbeitung

  1. temperatureAfter cooling to room temperature (rt)
  2. extractionthe mixture was extracted into ethyl acetate (EtOAc)
  3. washwashed with water, brine
  4. dry with materialdried with sodium sulfate (Na2SO4)
  5. customRemoval of the solvent and chromatography on silica
  6. washeluting with EtOAc/hexanes (1:20-1:10

Quellen und Nachweise

ORD-Eintrag
ord-48ec6b01a3864024ac16587c981afead
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728003B2

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