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

HRID 554071
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 554071
[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-ea906a4419bc41eb9c2c4ff7a3dd1224
Quelldatensatz
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08048907B2

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