Triethylamine → 3,3-Dimethyl-1-[2-(6-phenylhexanoyl)-perhydropyridazinyl]pentane-1,2-dione

HRID 2228457

Reaktionsgleichung

Reaktionsgleichung von HRID 2228457
C(N([CH2:6][CH3:7])CC)C.ClC([O:11][CH2:12][CH:13]([CH3:15])C)=O.[CH3:16][C:17]([CH3:30])([CH2:28][CH3:29])[C:18](=[O:27])[C:19]([CH:21]1[CH2:26][CH2:25][CH2:24][NH:23][NH:22]1)=[O:20]>C(Cl)Cl>[CH3:16][C:17]([CH3:30])([CH2:28][CH3:29])[C:18](=[O:27])[C:19]([CH:21]1[CH2:26][CH2:25][CH2:24][NH:23][N:22]1[C:12](=[O:11])[CH2:13][CH2:15][CH2:24][CH2:25][CH2:26][C:7]1[CH:6]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:20]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 694178043,3-Dimethyl-1-perhydropyridazinylpentane-1,2-dione

Produkt 1

HCID 184700683,3-Dimethyl-1-[2-(6-phenylhexanoyl)-perhydropyridazinyl]pentane-1,2-dioneAusbeute 103,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 5-phenylvalaric acid (0.2 g, 1.1 mmol) in 3 ml CH2Cl2 was added triethylamine (0.15 ml, 1.1 mmol), followed by isobutyl chloroformate (0.15 g, 1.1 mmol) at 0° C. After stirring for 5 minutes, a solution of 3,3-dimethyl-1-perhydropyridazinylpentane-1,2-dione (0.212 g, 1 mmol) in 1 ml CH2Cl2 was added. The reaction was gradually warmed up to room temperature. The crude material was subject to silica gel purification to yield final product as clear oil (0.20 g, 55%). Rf=0.58 (33% EtOAc/hexane). 1H NMR (CDCl3, 400 MHz): δ 0.89 (t, 3H, J=7.5); 1.24 (s, 6H); 1.37 (m, 2H); 1.68 (m, 6H); 1.74 (m, 4H); 2.23 (m, 2H); 2.62 (t, 2H, J=7.60); 2.80 (m, 2H); 4.53 (m, 2H); 7.21 (m, 5H). Anal. Calcd. for C23H24N2O3: C, 71.47; H, 8.87; N, 7.25. Found: C, 71.54; H, 8.80; N, 7.32.

Aufarbeitung

  1. customThe crude material was subject to silica gel purification

Quellen und Nachweise

ORD-Eintrag
ord-d19e15624d2d428fbe3c0acdcc27ce3c
Quelldatensatz
uspto-grants-2002_07
Patentnummer
US06417189B1

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