Water → (S)-1-(4-hydroxy-phenyl)-5-oxo-pyrrolidine-3-carboxylic acid methyl ester

HRID 859206Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 859206
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:13])[CH2:11][C@H:10]([C:14]([OH:16])=[O:15])[CH2:9]2)=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH3:22]OC(OC)(C)C.O>CO>[CH3:22][O:15][C:14]([C@H:10]1[CH2:11][C:12](=[O:13])[N:8]([C:5]2[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=2)[CH2:9]1)=[O:16]

Komponenten

6

Edukt 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 64952,2-DimethoxypropaneHCID 699443(3S)-1-(4-hydroxyphenyl)-5-oxopyrrolidine-3-carboxylic acid

Produkt 1

HCID 785701(S)-1-(4-hydroxy-phenyl)-5-oxo-pyrrolidine-3-carboxylic acid methyl esterAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 26 g (117.5 mmol) of (S)-1-(4-hydroxy-phenyl)-5-oxo-pyrrolidine-3-carboxylic acid, 0.66 ml of sulfuric acid, and 100 ml of dimethoxypropane in 700 ml of methanol are heated to reflux for 3 hours. For the working-up, the reaction mixture is reduced to ⅘ of its volume, then the residue is added under stirring to a mixture of ice and water. The precipitated product is collected on a filter funnel, washed with cold water and finally dried under high vacuum to yield 23.7 g (86% of theory) of (S)-1-(4-hydroxy-phenyl)-5-oxo-pyrrolidine-3-carboxylic acid methyl ester as a white solid; MS: m/e=234 (M−H)+; optical integrity: 97.4% e.e. .

Aufarbeitung

  1. temperatureare heated
  2. temperatureto reflux for 3 hours
  3. additionthe residue is added
  4. customThe precipitated product is collected on a filter funnel
  5. washwashed with cold water
  6. customfinally dried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-c5c5260ea62f4bf19eaf242a26c6e2f8
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07151111B2

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