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

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Reaktionsgleichung

[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

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

Tetrabutylammonium bromide (200 mg) was added to a mixture of 5-aminoindan (5 g, 37.6 mmol), ethyl 3-chloropropionate (4.7 mL, 37.6 mmol) and potassium carbonate (5.2 g, 37.6 mmol). 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

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

Quellen und Nachweise

ORD-Eintrag: ord-fad015707fc649399337ae5c3a962d56
Quelldatensatz: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07642270B2

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