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

HRID 2396787Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2396787
[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 tool) 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 a saturated ammonium chloride solution at -78° C, and then water was 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 a saturated ammonium chloride solution at -78° C
  4. additionwater was 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-0e411d8e6fe54150a26d9635fa417368
Quelldatensatz
uspto-grants-1996_02
Patentnummer
US05494925

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