Ethyl Acetate → Eslicarbazepine

HRID 872940Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 872940
[CH:1]1[CH:2]=[CH:3][C:4]2[N:16]([C:17]([NH2:19])=[O:18])[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:8](=[O:9])[CH2:7][C:5]=2[CH:6]=1.C(OCC)(=O)C.[OH-].C[N+](C)(C)C>CN(C)C=O.C(O)=O.O>[OH:9][C@@H:8]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=2[N:16]([C:17]([NH2:19])=[O:18])[C:4]2[CH:3]=[CH:2][CH:1]=[CH:6][C:5]=2[CH2:7]1

Komponenten

7

Edukt 3

HCID 8857Ethyl AcetateHCID 34312OxcarbazepineHCID 60966Tetramethylammonium hydroxide

Produkt 1

HCID 9881504Eslicarbazepine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 284Formic AcidLösungsmittel3×HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

In a 250 ml flask with thermometer, reflux condenser, stirrer and under nitrogen was added 8 g oxcarbazepine, 60 ml of ethyl acetate, 18 ml tetramethylammonium hydroxide (25% solution in water), 2 ml formic acid and 5 ml water. 21 mg RuCl [(S,S)-Ts-DPEN](p-cymene) (SigmaAldrich 703915) was dissolved in 5 ml dimethylformamide and added to the reaction. The reaction was heated in an oil bath to reflux. The pH was checked approximately every 30 to 60 minutes and formic acid added as required to about pH 5. In this way the pH was maintained between 5 and 9. After 7 hours the conversion was 80% and after overnight reaction without further formic acid addition a conversion (HPLC area % at 210 nm) of 96% was obtained with a product ee of 97.1% of (S)-(+)-10-hydroxy-10,11-dihydro-5H-dibenz[b,f]azepine-5-carboxamide (pH 8.5). The reaction was cooled on ice for 4 hours with stirring, filtered and washed 2 times with 20 ml methyl tert-butyl ether (MTBE) to yield 7.5 g alcohol after drying with a purity of 99,3% (HPLC ala %).

Aufarbeitung

  1. temperatureIn a 250 ml flask with thermometer, reflux condenser, stirrer
  2. additionadded to the reaction
  3. temperatureThe reaction was heated in an oil bath
  4. temperatureto reflux
  5. temperatureIn this way the pH was maintained between 5 and 9
  6. waitAfter 7 hours the conversion was
  7. custom80% and after overnight reaction

Quellen und Nachweise

ORD-Eintrag
ord-3c76a7fdbf8540449d5c904e6d36d8b6
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08975396B2

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