Triethylamine → HCID 66876110, Verbindung

HRID 1666525Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1666525
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.[OH:12][C:13]1[CH:14]=[C:15]([CH:30]=[CH:31][CH:32]=1)[CH:16]=[C:17]1[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]1.C(N(CC)CC)C>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:12][C:13]2[CH:14]=[C:15]([CH:30]=[CH:31][CH:32]=2)[CH:16]=[C:17]2[CH2:18][CH2:19][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:27])[CH3:28])=[O:24])[CH2:21][CH2:22]2)=[CH:5][CH:4]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 201262(4-Methoxyphenyl)boronic acidHCID 53485958Tert-butyl 4-(3-hydroxybenzylidene)piperidine-1-carboxylate

Produkt 1

HCID 66876110HCID 66876110, VerbindungAusbeute 32,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8895Cupric acetateKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a mixture of 4-methoxyphenylboronic acid (1.57 g, 10.36 mmole) and tert-butyl 4-(3-hydroxybenzylidene)piperidine-1-carboxylate (2.5 g, 8.6 mmole) in dichloromethane (75 mL) were added copper acetate (1.63 g, 8.6 mmole), triethyl amine (5.219 g, 51.6 mmol) and molecular sieves. The mixture was stirred at room temperature overnight. The reaction mixture was filtered through celite pad. The filtrate was evaporated and purified by column chromatography to give the title compound (1.1 g, 32%). 1H NMR (500 MHz, CDCl3): δ ppm 7.26 (t, 1H), 6.99 (d, 2H), 6.89 (t, 3H), 6.79 (t, 2H), 6.29 (s, 1H), 3.80 (s, 3H), 3.48 (s, 2H), 3.38 (s, 2H), 2.42 (s, 2H), 2.29 (s, 2H), 1.47 (s, 9H).

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through celite pad
  2. customThe filtrate was evaporated
  3. custompurified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-71a7903e805d45c59037bb8ff80871b0
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08044052B2

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