1-(tert-butyl) 2-methyl (2S)-4-hydroxypyrrolidine-1,2-dicarboxylate → 1-tert-butyl 2-methyl (2S)-4-oxopyrrolidine-1,2-dicarboxylate

HRID 345323Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 345323
[CH3:1][O:2][C:3](=[O:17])[C@@H:4]1[CH2:8][CH:7]([OH:9])[CH2:6][N:5]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl.CCOCC>[CH3:1][O:2][C:3](=[O:17])[C@@H:4]1[CH2:8][C:7](=[O:9])[CH2:6][N:5]1[C:10]([O:12][C:13]([CH3:15])([CH3:14])[CH3:16])=[O:11]

Komponenten

5

Edukt 2

HCID 121855781-(tert-butyl) 2-methyl (2S)-4-hydroxypyrrolidine-1,2-dicarboxylateHCID 178418287HCID 178418287, Verbindung

Produkt 1

HCID 109884851-tert-butyl 2-methyl (2S)-4-oxopyrrolidine-1,2-dicarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 12.7 g of N-t-butoxycarbonyl-4-hydroxyproline methyl ester and 44.7 g of pyridinium chlorochromate in 150 ml of methylene chloride is stirred at room temperature for 30 hours, diluted with 200 ml of ether and filtered through Florisil washing with ether (500 ml). The solution is evaporated to dryness, the residue is purified by flash chromatography on silica gel using ethyl acetate/hexane (40:60) as eluant to give N-t-butoxycarbonyl-4-oxoproline methyl ester.

Aufarbeitung

  1. filtrationfiltered through Florisil washing with ether (500 ml)
  2. customThe solution is evaporated to dryness
  3. customthe residue is purified by flash chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-7651f837810747ccb6f2c7b226788bfa
Quelldatensatz
uspto-grants-1991_10
Patentnummer
US05057506

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