Trifluoroacetic acid → (5R)-5-(1-ethoxyethoxymethyl)pyrrolidin-2-one

HRID 22965

Reaktionsgleichung

Reaktionsgleichung von HRID 22965
[OH:1][CH2:2][C@@H:3]1[NH:7][C:6](=[O:8])[CH2:5][CH2:4]1.[CH:9]([O:11][CH2:12][CH3:13])=[CH2:10].FC(F)(F)C(O)=O>C(Cl)(Cl)Cl>[CH2:9]([O:11][CH:12]([O:1][CH2:2][C@@H:3]1[NH:7][C:6](=[O:8])[CH2:5][CH2:4]1)[CH3:13])[CH3:10]

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 8023Ethyl vinyl etherHCID 7128291(R)-(-)-5-(Hydroxymethyl)-2-pyrrolidinone

Produkt 1

HCID 12137689(5R)-5-(1-ethoxyethoxymethyl)pyrrolidin-2-oneAusbeute 102 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

To a solution of (5R)-5-(hydroxymethyl)pyrrolidin-2-one (Aldrich, 8.86 g, 77 mmol) in 70 mL of chloroform at room temperature under an argon atmosphere was added ethyl vinyl ether (10.4 mL, 108 mmol) and catalytic anhydrous trifluoroacetic acid (0.2 mL). After stirring for 3 hours, the reaction was partitioned between methylene chloride (150 mL) and aqueous sodium bicarbonate solution (150 mL) and the phases were separated. The organic phase was dried (K2CO3) and filtered. The filtrate was evaporated under reduced pressure to give 14.7 g of the (5R)-5-(1-ethoxyethoxymethyl)pyrrolidin-2-one.

Aufarbeitung

  1. customthe reaction was partitioned between methylene chloride (150 mL) and aqueous sodium bicarbonate solution (150 mL)
  2. customthe phases were separated
  3. dry with materialThe organic phase was dried (K2CO3)
  4. filtrationfiltered
  5. customThe filtrate was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-a33fe86201f24b20b09fad2d95879b46
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06849657B2

Verknüpfte Notizen

Wird geladen…