Benzyl Bromide → (S)-(+)-1-Benzyl-5-ethoxycarbonylpyrrolidin-2-one

HRID 2211585Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2211585
[NH:1]1[C@H:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:4][CH2:3][C:2]1=[O:11].[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(O[K])(C)(C)C.O.CCOC(C)=O>C1COCC1>[CH2:9]([O:8][C:6](=[O:7])[C@@H:5]1[CH2:4][CH2:3][C:2](=[O:11])[N:1]1[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH3:10]

Komponenten

6

Edukt 4

HCID 7498Benzyl BromideHCID 2724446Ethyl 5-oxo-L-prolinateHCID 22728543Water ethylacetateHCID 178418922HCID 178418922, Verbindung

Produkt 1

HCID 11064735(S)-(+)-1-Benzyl-5-ethoxycarbonylpyrrolidin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Ethyl (S)-(+)-2-pyrrolidone-5-carboxylate (1 g, 6.36 mmol) and benzyl bromide (0.76 mL, 6.36 mmol) were placed in dry THF (30 mL). The reaction mixture was stirred and cooled to 0° C. A 1M solution of tert-BuOK was added dropwise (6.36 ML, 6.36 mmol) and the reaction was stirred for an additional 0.5 h at 0° C. and allowed to come to room temperate where it was stirred for 24 hours under N2. The reaction was then dissolved into a 1:1 mixture of H2O/EtOAc. The organic layer was washed with 1M HCl, H2O and brine, and then dried over MgSO4 to afford N-benzyl-L-pyroglutamic acid ethyl ester an oil.

Aufarbeitung

  1. stirringthe reaction was stirred for an additional 0.5 h at 0° C.
  2. stirringwas stirred for 24 hours under N2
  3. washThe organic layer was washed with 1M HCl, H2O and brine
  4. dry with materialdried over MgSO4

Quellen und Nachweise

ORD-Eintrag
ord-ca231b3add9545b78b96b69161149a24
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07101855B2

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