Potassium Carbonate → HCID 54561569, Verbindung

HRID 1683738Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1683738
[CH:1](=[C:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C:9]1=[N:14][OH:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br.[CH2:17]([O:19][C:20]([C@@H:22]1[CH2:27][CH2:26][CH2:25][N:24]([CH2:28][CH2:29]Br)[CH2:23]1)=[O:21])[CH3:18].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:17]([O:19][C:20]([C@@H:22]1[CH2:27][CH2:26][CH2:25][N:24]([CH2:28][CH2:29][O:15][N:14]=[C:9]2[CH2:10][CH2:11][CH2:12][CH2:13][C:8]2=[CH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:23]1)=[O:21])[CH3:18]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 189199HCID 189199, VerbindungHCID 70009171(R)-1-(2-bromoethyl)nipecotic acid ethyl ester hydrobromide

Produkt 1

HCID 54561569HCID 54561569, VerbindungAusbeute 35,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A mixture of the above oxime (3.7 g, 18.4 mmol), (R)-1-(2-bromoethyl)-3-piperidinecarboxylic acid ethyl ester hydrobromide (7.0 g, 20.2 mmol, EP 374801), potassium carbonate (10.2 g, 73.5 mmol) and acetone (150 ml) was stirred at ambient temperature for 11 days. The mixture was filtered and the solvent evaporated in vacuo. The residue was purified by column chromatography on silica gel (200 g, heptane/ethyl acetate=3/2) to give 2.5 g of (R)-1-(2-(((2-(benzylidene)cyclohexylidene)amino)oxy)ethyl)-3-piperidinecarboxylic acid ethyl ester as an oil.

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. customthe solvent evaporated in vacuo
  3. customThe residue was purified by column chromatography on silica gel (200 g, heptane/ethyl acetate=3/2)

Quellen und Nachweise

ORD-Eintrag
ord-6a0a6e53df27443294320ae09860f0a5
Quelldatensatz
uspto-grants-1997_06
Patentnummer
US05639766

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