Sulfuric Acid → 4-(Hydroxymethyl)-1-methylpyrrolidin-2-one

HRID 1834808Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1834808
[Li+].[BH4-].[C:3]([CH:7]1[CH2:11][N:10]([CH3:12])[C:9](=[O:13])[CH2:8]1)(OC)=[O:4].S(=O)(=O)(O)O>C(OCC)C>[OH:4][CH2:3][CH:7]1[CH2:11][N:10]([CH3:12])[C:9](=[O:13])[CH2:8]1

Komponenten

5

Edukt 3

HCID 1118Sulfuric AcidHCID 1084021-Methyl-5-oxo-pyrrolidine-3-carboxylic acid methyl esterHCID 4148881Lithium borohydride

Produkt 1

HCID 219142634-(Hydroxymethyl)-1-methylpyrrolidin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

A solution of 2.3g (106 m moles) of LiBH4 in 150 ml of diethyl ether was slowly added dropwise at +5° C to 17.0g (107 m mols) of 4-carbomethoxy-1-methyl-pyrrolidone in 20 ml of absolute diethyl ether. Stirring was continued for 2 hours at room temperature, then the mixture was acidified with 2N sulfuric acid (pH 2), the solvent and water were distilled off to a large extent in vacuo and the remaining residue was extracted with methylene chloride. The dried methylene chloride phase was concentrated and the residue was distilled in vacuo. 5 g of the compounds desired were obtained in a 98 % purity: nD20 : 1.4950.

Aufarbeitung

  1. distillationthe solvent and water were distilled off to a large extent in vacuo
  2. extractionthe remaining residue was extracted with methylene chloride
  3. concentrationThe dried methylene chloride phase was concentrated
  4. distillationthe residue was distilled in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-4332e064dc1744829d6ee52788002db0
Quelldatensatz
uspto-grants-1978_01
Patentnummer
US04071530

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