Sodium Hydroxide → 2-[6-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)pyridin-2-ylcarbamoyl]morpholine-4-carboxylic acid tert-butyl ester

HRID 1401868Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1401868
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([C:14]([OH:16])=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OC1C=CC2C(=CC=CC=2)N1C(OCC)=O)C.[CH3:35][C:36]1([CH3:55])[CH2:45][CH2:44][C:43]([CH3:47])([CH3:46])[C:42]2[CH:41]=[C:40]([C:48]3[N:53]=[C:52]([NH2:54])[CH:51]=[CH:50][CH:49]=3)[CH:39]=[CH:38][C:37]1=2.[OH-].[Na+]>C1COCC1.O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([C:14](=[O:16])[NH:54][C:52]2[CH:51]=[CH:50][CH:49]=[C:48]([C:40]3[CH:39]=[CH:38][C:37]4[C:36]([CH3:55])([CH3:35])[CH2:45][CH2:44][C:43]([CH3:47])([CH3:46])[C:42]=4[CH:41]=3)[N:53]=2)[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Komponenten

7

Edukt 4

HCID 14798Sodium HydroxideHCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 27559654-((Tert-butoxy)carbonyl)morpholine-2-carboxylic acidHCID 673240416-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)pyridin-2-ylamine

Produkt 1

HCID 673232752-[6-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)pyridin-2-ylcarbamoyl]morpholine-4-carboxylic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

82 mg (0.36 mmol) of morpholine-2,4-dicarboxylic acid 4-tert-butyl ester and 97 mg (0.39 mmol) of ethyl 2-ethoxy-1,2-dihydroquinoline-1-carboxylate (EEDQ) are suspended in 2 ml of THF and stirred at room temperature for 20 min. 100 mg (0.36 mmol) of 6-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)pyridin-2-ylamine from step a are added to the mixture. The mixture is stirred further overnight, water is added, the mixture is adjusted to pH 9-10 using a 2N NaOH solution and extracted twice with EA. The combined organic phases are dried, filtered and evaporated (191 mg). The residue is purified by means of flash chromatography on silica gel.

Aufarbeitung

  1. stirringThe mixture is stirred further overnight
  2. extractionextracted twice with EA
  3. customThe combined organic phases are dried
  4. filtrationfiltered
  5. customevaporated (191 mg)
  6. customThe residue is purified by means of flash chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-cecd65411c414631b210db514b9a7695
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08907098B2

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