3-Hydroxyquinoline → HCID 21309661, Verbindung

HRID 617348

Reaktionsgleichung

Reaktionsgleichung von HRID 617348
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[CH2:13][OH:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].O[C:16]1[CH:17]=[N:18][C:19]2[C:24]([CH:25]=1)=[CH:23][CH:22]=[CH:21][CH:20]=2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[CH2:13][O:14][C:16]1[CH:17]=[N:18][C:19]2[C:24]([CH:25]=1)=[CH:23][CH:22]=[CH:21][CH:20]=2)([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7]

Komponenten

6

Edukt 4

HCID 113763-HydroxyquinolineHCID 11776TriphenylphosphineHCID 688279N-(tert-Butoxycarbonyl)-D-prolinolHCID 5462977Diethyl azodicarboxylate

Produkt 1

HCID 21309661HCID 21309661, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A 2.77 g sample of (R)-1-t-butoxycarbonyl-2-pyrrolidinemethanol and 3 g of 3-hydroxyquinoline were reacted with triphenylphosphine and DEAD in 100 mL of THF according to the procedure of Example 14a, to give 2.5 g of the title compound. MS (DCI/NH3) m/e 329 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ: 8.67 (d, J=3 Hz 1H), 8.4 (d, J=7 Hz, 1H), 7.72 (dd, J=7, 1 Hz 1H), 7.56-7.40 (m, 3H), 4.24-3.94 (m, 3 H), 3.42 (bs 2H), 2.11-1.94 (m 3H), 1.92-1.48 (m 1H), (s 9H).

Quellen und Nachweise

ORD-Eintrag
ord-80448b942d2e43a8918365bfd7098250
Quelldatensatz
uspto-grants-1999_09
Patentnummer
US05948793

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