Tetrahydrofuran → N-Cyclobutylacetyl-4-benzyl-2-oxazolidinone

HRID 52834

Reaktionsgleichung

Reaktionsgleichung von HRID 52834
[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[NH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:14]([Li])[CH2:15][CH2:16][CH3:17].[O:19]1CC[CH2:21][CH2:20]1>C(Cl)(Cl)Cl>[CH:17]1([CH2:21][C:20]([N:9]2[CH:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:12][O:11][C:10]2=[O:13])=[O:19])[CH2:16][CH2:15][CH2:14]1

Komponenten

5

Edukt 3

HCID 8028TetrahydrofuranHCID 736225(S)-4-Benzyl-2-oxazolidinoneHCID 178418339Butyllithium

Produkt 1

HCID 21180756N-Cyclobutylacetyl-4-benzyl-2-oxazolidinoneAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

To (S)(-)-4-benzyl-2-oxazolidinone (2.65 g, 1.8 equiv) dissolved in tetrahydrofuran (25 mL) at -78° C. was added 2.5M butyl lithium (5.98 mL, 1.8 equiv). After 5 minutes, this solution was cannulated into the above solution. The reaction mixture was allowed to come to room temperature and stirred for 2 hours. The reaction mixture was diluted with Chloroform (150 mL), washed with 10% sodium bisulfite (100 mL), dried over sodium sulfate, and concentrated under reduced pressure. The residue obtained was chromatographed on silica gel eluting with 3:2 hexane/ethyl acetate to afford the title compound in 58% yield.

Aufarbeitung

  1. customto come to room temperature
  2. washwashed with 10% sodium bisulfite (100 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue obtained
  6. customwas chromatographed on silica gel eluting with 3:2 hexane/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-3a9e37f27d224dd895b0fb94db23dd32
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05616714

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