Chlorotrimethylsilane → 1-(Pyrrolidin-1-yl)cyclopropanecarbonitrile

HRID 496067

Reaktionsgleichung

Reaktionsgleichung von HRID 496067
C[Si](Cl)(C)C.C(O[C:9]1(O[Si](C)(C)C)[CH2:11][CH2:10]1)C.Cl.[NH:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1.[C-:23]#[N:24].[K+]>CO>[N:18]1([C:9]2([C:23]#[N:24])[CH2:10][CH2:11]2)[CH2:22][CH2:21][CH2:20][CH2:19]1

Komponenten

6

Edukt 4

HCID 6397ChlorotrimethylsilaneHCID 9032Potassium CyanideHCID 212848Pyrrolidine, hydrochloride (1:1)HCID 2734686(1-Ethoxycyclopropoxy)trimethylsilane

Produkt 1

HCID 223251461-(Pyrrolidin-1-yl)cyclopropanecarbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

A mixture containing a drop of trimethylsilyl chloride and 67.8 g of [(1-ethoxycyclopropyl)oxy]trimethylsilane in 65 ml of methanol is added to 62.6 g of pyrrolidine hydrochloride and 28.7 g of potassium cyanide dissolved in 260 ml of methanol. After stirring for 20 minutes at 20° C., and then for 20 hours at 50° C., the reaction mixture is concentrated to dryness, taken up in dichloromethane, filtered and concentrated to dryness again. The residue is chromatographed over silica gel (CH2Cl2) allowing the desired product to be isolated.

Aufarbeitung

  1. waitfor 20 hours at 50° C.
  2. concentrationthe reaction mixture is concentrated to dryness
  3. filtrationfiltered
  4. concentrationconcentrated to dryness again
  5. customThe residue is chromatographed over silica gel (CH2Cl2)
  6. customto be isolated

Quellen und Nachweise

ORD-Eintrag
ord-bdc44c5517794472b5931f634f1b8229
Quelldatensatz
uspto-grants-2005_09
Patentnummer
US06943184B2

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