Potassium Carbonate → (R)-1-(2-(((2-phenylcyclohex-2-enylidene)amino)oxy)ethyl)-3-piperidinecarboxylic acid ethyl ester

HRID 1683735Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1683735
[C:1]1([C:7]2[C:8](=[N:13][OH:14])[CH2:9][CH2:10][CH2:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br.[CH2:16]([O:18][C:19]([C@@H:21]1[CH2:26][CH2:25][CH2:24][N:23]([CH2:27][CH2:28]Br)[CH2:22]1)=[O:20])[CH3:17].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:16]([O:18][C:19]([C@@H:21]1[CH2:26][CH2:25][CH2:24][N:23]([CH2:27][CH2:28][O:14][N:13]=[C:8]2[CH2:9][CH2:10][CH2:11][CH:12]=[C:7]2[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:22]1)=[O:20])[CH3:17]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 604484N-(2-phenylcyclohex-2-en-1-ylidene)hydroxylamineHCID 70009171(R)-1-(2-bromoethyl)nipecotic acid ethyl ester hydrobromide

Produkt 1

HCID 54444134(R)-1-(2-(((2-phenylcyclohex-2-enylidene)amino)oxy)ethyl)-3-piperidinecarboxylic acid ethyl esterAusbeute 37,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A mixture of the above oxime (0.55 g, 2.9 mmol), (R)-1-(2-bromoethyl)-3-piperidinecarboxylic acid ethyl ester hydrobromide (1.0 g, 2.9 mmol, EP 374801A), potassium carbonate (1.0 g, 7.3 mmol) and acetone (25 ml) was stirred at ambient temperature for 14 days. The mixture was filtered and the solvent evaporated in vacuo. The residue was purified by column chromatography on silica gel (125 g, heptane/ethyl acetate=1/1) to give 0.4 g of (R)-1-(2-(((2-phenylcyclohex-2-enylidene)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 (125 g, heptane/ethyl acetate=1/1)

Quellen und Nachweise

ORD-Eintrag
ord-ffe373932e374bbb8dee875c316b1ec0
Quelldatensatz
uspto-grants-1997_06
Patentnummer
US05639766

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