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Methanol → (S)-1-isopropyl-5-oxopyrrolidine-2-carboxylic acid

HRID 2238477
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2238477
[CH3:1][CH:2]([N:4]1[C:12](=[O:13])[CH2:11][CH2:10][C@H:5]1[C:6]([O:8]C)=[O:7])[CH3:3].CO.[OH-].[Na+]>O>[CH3:3][CH:2]([N:4]1[C:12](=[O:13])[CH2:11][CH2:10][C@H:5]1[C:6]([OH:8])=[O:7])[CH3:1]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 67461795methyl (2S)-5-oxo-1-(propan-2-yl)pyrrolidine-2-carboxylate

Produkt 1

HCID 18649401(S)-1-isopropyl-5-oxopyrrolidine-2-carboxylic acidAusbeute 42,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Methyl 1-(1-methylethyl)-5-oxo-prolinate (0.152 g, 0.82 mmol) was dissolved in water (3 ml) and methanol (0.5 ml) and treated with 2M aqueous sodium hydroxide (0.682 ml, 1.36 mmol). The mixture was stirred for ˜4 hrs at room temperature and then washed with dichloromethane. The aqueous layer was evaporated and the residue treated with an excess of 1M hydrogen chloride in ether (˜5 ml). The mixture was evaporated once more and the residue was triturated with dichloromethane. The solid material was discarded and the combined dichloromethane fractions were evaporated to give 1-(1-methylethyl)-5-oxo-proline (0.060 g) as a yellow oil which crystallized on standing.

Aufarbeitung

  1. washwashed with dichloromethane
  2. customThe aqueous layer was evaporated
  3. additionthe residue treated with an excess of 1M hydrogen chloride in ether (˜5 ml)
  4. customThe mixture was evaporated once more
  5. customthe residue was triturated with dichloromethane
  6. customthe combined dichloromethane fractions were evaporated

Quellen und Nachweise

ORD-Eintrag
ord-17cd0fa115224fcaaa4e28bbca942dee
Quelldatensatz
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07718693B2

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