5-Iodo-2-tritylisoindoline → tert-Butyl 2,2-dimethyl-5-((6-(oct-1-ynyl)-3,4-dihydroquinolin-1(2H)-yl)methyl)-1,3-dioxan-5-ylcarbamate

HRID 710307

Reaktionsgleichung

Reaktionsgleichung von HRID 710307
I[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][C:13]1([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:18][O:17][C:16]([CH3:20])([CH3:19])[O:15][CH2:14]1)[CH2:7][CH2:6][CH2:5]2.I[C:30]1[CH:31]=[C:32]2[C:36](=[CH:37][CH:38]=1)[CH2:35]N(C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:33]2>>[CH3:19][C:16]1([CH3:20])[O:15][CH2:14][C:13]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])([CH2:12][N:8]2[C:9]3[C:4](=[CH:3][C:2]([C:33]#[C:32][CH2:31][CH2:30][CH2:38][CH2:37][CH2:36][CH3:35])=[CH:11][CH:10]=3)[CH2:5][CH2:6][CH2:7]2)[CH2:18][O:17]1

Komponenten

3

Edukt 2

HCID 667262485-Iodo-2-tritylisoindolineHCID 86661764tert-Butyl 5-((6-iodo-3,4-dihydroquinolin-1(2H)-yl)methyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate

Produkt 1

HCID 86661763tert-Butyl 2,2-dimethyl-5-((6-(oct-1-ynyl)-3,4-dihydroquinolin-1(2H)-yl)methyl)-1,3-dioxan-5-ylcarbamateAusbeute 35 %

Versuchsvorschrift

When the product of Step B is substituted for 5-iodo-2-tritylisoindoline in Example 2, Step D, the identical process afforded the title compound in 35% yield, as a brownish foam. 1H-NMR (CDCl3) 0.88 (m, 3H); 1.41 (m, 8H); 1.50 (m, 2H); 1.87 (m, 2H); 2.34 (tr, 2H, J=7.0 Hz); 2.72 (tr, 2H, J=6.3 Hz); 3.26-3.32 (m, 2H); 3.69 (5, 2H); 3.9 (s, 3H); 4.65 (s, 1H); 6.68 (d, 1H, J=8.7 Hz); 6.98 (s, 1H); 7.04 (d, 1H, J=8.7 Hz).

Quellen und Nachweise

ORD-Eintrag
ord-b3c7c6ec40804c1a9a84b67fcc90caa8
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181182B2

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