Tetrahydrofuran → HCID 86602285, Verbindung

HRID 504384Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 504384
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:9]=[C:10]1[CH2:14][N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C@H:12]([C:22]([O:24][CH3:25])=[O:23])[CH2:11]1.O1CCCC1>CCOCC>[OH:9][C:10]1([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:14][N:13]([C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16])[C@H:12]([C:22]([O:24][CH3:25])=[O:23])[CH2:11]1

Komponenten

5

Edukt 3

HCID 8028TetrahydrofuranHCID 109884851-tert-butyl 2-methyl (2S)-4-oxopyrrolidine-1,2-dicarboxylateHCID 178418255HCID 178418255, Verbindung

Produkt 1

HCID 86602285HCID 86602285, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

Phenylmagnesium bromide in ether (3.00M, 0.400 mL) was added to a solution of 1-tert-butyl 2-methyl (2S)-4-oxopyrrolidine-1,2-dicarboxylate (243.0 mg, 0.0009989 mol) in tetrahydrofuran (5.00 mL, 0.0616 mol) at −40° C. The reaction mixture was stirred at between −40° C. and −10° C. for 2 h and then was quenched with ammonium chloride solution (5 mL). The organic phase was separated and the aqueous phase was extracted with ethyl acetate (2×5 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was used directly in the next step without further purification.

Aufarbeitung

  1. customwas quenched with ammonium chloride solution (5 mL)
  2. customThe organic phase was separated
  3. extractionthe aqueous phase was extracted with ethyl acetate (2×5 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was used directly in the next step without further purification

Quellen und Nachweise

ORD-Eintrag
ord-818b7a5f53c94c2c9f1f546e480c900f
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07776874B2

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