Pyridine → 2-(2-Oxopyrrolidin-1-yl)ethyl 4-methylbenzenesulfonate

HRID 237479

Reaktionsgleichung

Reaktionsgleichung von HRID 237479
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[OH:12][CH2:13][CH2:14][N:15]1[CH2:19][CH2:18][CH2:17][C:16]1=[O:20].N1C=CC=CC=1>ClCCl>[CH3:11][C:1]1[CH:6]=[CH:5][C:4]([S:7]([O:12][CH2:13][CH2:14][N:15]2[CH2:19][CH2:18][CH2:17][C:16]2=[O:20])(=[O:9])=[O:8])=[CH:3][CH:2]=1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 769801-(2-Hydroxyethyl)-2-pyrrolidinone

Produkt 1

HCID 447912072-(2-Oxopyrrolidin-1-yl)ethyl 4-methylbenzenesulfonate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

p-Toluenesulfonylchloride (1 g) is added portionwise to a solution of 1-(2-hydroxyethyl)pyrrolidin-2-one (500 μL) and pyridine (1.5 mL) in dichloromethane (8 mL) chilled in an ice bath. The mixture is stirred at room temperature for 12 hours and partitioned between 1 M hydrochloric acid and diethylether. The organic phase is dried (MgSO4) and concentrated. The residue is chromatographed on silica gel (ethyl acetate) to give the title compound. Yield: 390 mg; Mass spectrum (ESI+): m/z=284 [M+H]+.

Aufarbeitung

  1. temperaturechilled in an ice bath
  2. custompartitioned between 1 M hydrochloric acid and diethylether
  3. dry with materialThe organic phase is dried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue is chromatographed on silica gel (ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-4062c828a452496db321125cd9fbf4e9
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642585B2

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