2-Butene, 1-bromo-3-methyl- → HCID 18922258, Verbindung

HRID 743463Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 743463
[Li+].CC([N-]C(C)C)C.[CH3:9][O:10][C:11](=[O:22])[CH2:12][N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH3:14].Br[CH2:24][CH:25]=[C:26]([CH3:28])[CH3:27]>C1COCC1>[CH3:9][O:10][C:11](=[O:22])[CH:12]([CH2:24][CH:25]=[C:26]([CH3:28])[CH3:27])[N:13]([C:15]([O:17][C:18]([CH3:19])([CH3:21])[CH3:20])=[O:16])[CH3:14]

Komponenten

5

Edukt 3

HCID 700922-Butene, 1-bromo-3-methyl-HCID 2724682Lithium diisopropylamideHCID 14018930Methyl 2-((tert-butoxycarbonyl)(methyl)amino)acetate

Produkt 1

HCID 18922258HCID 18922258, VerbindungAusbeute 63,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A 2 M solution of LDA (70.32 ml, 0.14 mol) was added (via syringe) to a solution of N-t-butoxycarbonyl-sarcosine methyl ester (26 g, 0.1279 mol) in 40 ml of dry THF at -78° C. under nitrogen and the mixture was stirred at this temperature for 30 minutes. To the above mixture was added 4-bromo-2-methyl-2-butene (20 g, 0.134 mol) with stirring continuing at -78° C., and the resulting mixture was allowed to warm to room temperature. The reaction mixture was quenched with 6 ml of saturated ammonium chloride solution at -78° C., 20 ml of water added, and the resulting reaction mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, dried over sodium sulfate, and concentrated in vacuo to yield a yellow oil, which was purified by silica gel column chromatography (20% ethyl acetate in hexane) to afford 22.1 g (63.7 %) of N-t-butoxycarbonyl-2-(3-methyl-2-butenyl)-sarcosine methyl ester as an oil.

Aufarbeitung

  1. stirringwith stirring
  2. customcontinuing at -78° C.
  3. customThe reaction mixture was quenched with 6 ml of saturated ammonium chloride solution at -78° C.
  4. addition20 ml of water added
  5. customthe resulting reaction mixture
  6. extractionwas extracted with ethyl acetate
  7. washThe organic layer was washed with water and brine
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated in vacuo
  10. customto yield a yellow oil, which
  11. customwas purified by silica gel column chromatography (20% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-4bad613defb3489ba9fbc7e755afd53e
Quelldatensatz
uspto-grants-1996_09
Patentnummer
US05556909

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