(2S,4R)-4-Hydroxypyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester → 1-tert-butyl 2-methyl (2S)-4-oxopyrrolidine-1,2-dicarboxylate

HRID 490125Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 490125
[OH:1][C@H:2]1[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@H:4]([C:14]([O:16][CH3:17])=[O:15])[CH2:3]1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)(Cl)Cl>[O:1]=[C:2]1[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:11])([CH3:12])[CH3:13])=[O:8])[C@H:4]([C:14]([O:16][CH3:17])=[O:15])[CH2:3]1

Komponenten

4

Edukt 2

HCID 2734883(2S,4R)-4-Hydroxypyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl esterHCID 178418287HCID 178418287, Verbindung2×

Produkt 1

HCID 109884851-tert-butyl 2-methyl (2S)-4-oxopyrrolidine-1,2-dicarboxylateAusbeute 132,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

150 g of 1-tert-butyl 2-methyl(2S,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate, 264 g of pyridinium chlorochromate, and 75 g of celite were stirred in 2 L of chloroform at room temperature. During this stirring, another 100 g of pyridinium chlorochromate was added, and the reaction mixture was stirred for a total of 7 days. The reaction solution was filtered through celite (washed with 500 mL of chloroform), and the filtrate was concentrated under reduced pressure to obtain 197 g of black oil. The residue thus obtained was purified by column chromatography (silica gel 60, mobile phase: ethyl acetate/n-hexane=2/1; v/v) to obtain 119 g of the titled compound (yellow oily substance).

Aufarbeitung

  1. filtrationThe reaction solution was filtered through celite (washed with 500 mL of chloroform)
  2. concentrationthe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-c1b9b4cce1f24942a441f3085e1994b5
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07528124B2

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