Water → cis 1-Ethoxycarbonyl-2-ethoxycarbonylpyrrolidine-3-ethanol

HRID 1587339Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1587339
[CH2:1]([O:3][C:4]([N:6]1[CH2:10][CH2:9][CH:8]([CH2:11][C:12](O)=[O:13])[CH:7]1[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:5])[CH3:2].B.O1CCCC1.O>O1CCCC1>[CH2:1]([O:3][C:4]([N:6]1[CH2:10][CH2:9][C@H:8]([CH2:11][CH2:12][OH:13])[C@@H:7]1[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:5])[CH3:2]

Komponenten

5

Edukt 3

HCID 962WaterHCID 2723981Borane;tetrahydrofuranHCID 197578301-Ethoxycarbonyl-2-ethoxycarbonyl-pyrrolidine-3-acetic acid

Produkt 1

HCID 86743786cis 1-Ethoxycarbonyl-2-ethoxycarbonylpyrrolidine-3-ethanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 10 g of 1-ethoxycarbonyl-2-ethoxycarbonyl-pyrrolidine-3-acetic acid in 50 ml tetrahydrofuran is cooled to 0° and 55 ml of borane/tetrahydrofuran (1M) is added dropwise. After stirring 2 hours at 0°, 20 ml of water is added, the mixture is extracted with ethyl acetate, washed twice with water and dried over sodium sulfate. The solution is filtered, concentrated and purified by flash chromatography using ethyl acetate/hexane (1:1 to 7:3) to yield cis 1-ethoxycarbonyl-2-ethoxycarbonylpyrrolidine-3-ethanol.

Aufarbeitung

  1. extractionthe mixture is extracted with ethyl acetate
  2. washwashed twice with water
  3. dry with materialdried over sodium sulfate
  4. filtrationThe solution is filtered
  5. concentrationconcentrated
  6. custompurified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-cbb06b82112f4b9ebf63b5cd9c68c183
Quelldatensatz
uspto-grants-1993_06
Patentnummer
US05217963

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