Ethyl benzoylacetate → (8-Ethyl-1-phenyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)-acetic acid ethyl ester

HRID 268669

Reaktionsgleichung

Reaktionsgleichung von HRID 268669
[CH2:1]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[NH:10][CH:9]=[C:8]2[CH2:12][CH2:13][OH:14])[CH3:2].N1C2C(=CC=CC=2)C(CCO)=C1.[C:27]([CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])(=O)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>>[CH2:39]([O:38][C:36](=[O:37])[CH2:35][C:27]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:9]2[NH:10][C:11]3[C:7]([C:8]=2[CH2:12][CH2:13][O:14]1)=[CH:6][CH:5]=[CH:4][C:3]=3[CH2:1][CH3:2])[CH3:40]

Komponenten

4

Edukt 3

HCID 7170Ethyl benzoylacetateHCID 10685TryptopholHCID 1982317-Ethyltryptophol

Produkt 1

HCID 69194982(8-Ethyl-1-phenyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)-acetic acid ethyl ester

Versuchsvorschrift

Following the procedure of example 22.A. except using 2-(7-ethyl-1H-indol-3-yl)-ethanol as the 3-indolethanol component and ethyl benzoylacetate as ketone component afforded the title compound as a solid. 1H NMR (500 MHz, CDCl3) δ 10.05 (br, 1H), 7.42 (d, 1H), 7.28 (m, 5H), 7.12 (m, 2H), 3.96 (m, 3H), 3.60 (m, 1H), 3.43 (d, 1H), 3.22 (d, 1H), 3.05 (m, 3H), 2.65 (dd, 1H), 1.42 (d, 3H), 1.03 (t, 3H); ESI (−) MS m/e=362 (MH−).

Quellen und Nachweise

ORD-Eintrag
ord-ab23b1e01f2842b6a6dd38dabcb7e0f1
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07446122B2

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