Chlorotrimethylsilane → 1-(8-Methyl-8-azabicyclo[3.2.1]oct-2-en-2-yl)ethan-1-one

HRID 2226155Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2226155
[C@@H:1]12[N:8]([CH3:9])[C@@H:5]([CH2:6][CH2:7]1)[CH2:4][CH:3]=[C:2]2[C:10]([O:12]CC)=O.[Si](Cl)(C)(C)[CH3:16].[Li]C>C1COCC1>[CH3:9][N:8]1[CH:5]2[CH2:6][CH2:7][CH:1]1[C:2]([C:10](=[O:12])[CH3:16])=[CH:3][CH2:4]2

Komponenten

5

Edukt 3

HCID 6397ChlorotrimethylsilaneHCID 25222744Ecgonidine ethyl esterHCID 178418348HCID 178418348, Verbindung

Produkt 1

HCID 5857561-(8-Methyl-8-azabicyclo[3.2.1]oct-2-en-2-yl)ethan-1-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-100 °C

Versuchsvorschrift

To a mixture of ethyl trop-2-ene-2-carboxylate (3.43 g, 0.019 mol) and Me3SiCl (10.32 g, 0.095 mol) in THF (70 mL) cooled to -100° C., MeLi (1.4 M, 17.07 n%L, 0.0239 mol) was added dropwise. After warming up to room temperature, the reaction mixture was stirred for 16 hours. Excess Me3SiCl and THF was evaporated off and the resulting residue was stirred with EtOH (6 mL) followed by water (6 mL). The mixture was then made acidic (6N HCl )and extracted with ether. The aqueous layer was made basic (solid K2CO3)and extracted with chloroform, dried (K2CO3) and concentrated to give

Aufarbeitung

  1. temperatureAfter warming up to room temperature
  2. customExcess Me3SiCl and THF was evaporated off
  3. stirringthe resulting residue was stirred with EtOH (6 mL)
  4. extractionmade acidic (6N HCl )and extracted with ether
  5. extractionextracted with chloroform
  6. dry with materialdried (K2CO3)
  7. concentrationconcentrated
  8. customto give

Quellen und Nachweise

ORD-Eintrag
ord-ae26fdafb80b4b869101bcd29f8dbee7
Quelldatensatz
uspto-grants-1994_09
Patentnummer
US05346911

Notizen zur Reaktion

Wird geladen…