Pyridine → N-nitroso-N-(tert-butoxycarbonyl)amino-cyclopropane

HRID 12820

Reaktionsgleichung

Reaktionsgleichung von HRID 12820
F[B-](F)(F)F.[N:6]#[O+:7].[C:8]([O:12][C:13]([NH:15][CH:16]1[CH2:18][CH2:17]1)=[O:14])([CH3:11])([CH3:10])[CH3:9].N1C=CC=CC=1.CCOC(C)=O>C(#N)C>[N:6]([N:15]([CH:16]1[CH2:18][CH2:17]1)[C:13]([O:12][C:8]([CH3:11])([CH3:9])[CH3:10])=[O:14])=[O:7]

Komponenten

6

Edukt 4

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 11137142Nitrilooxonium tetrafluoroborateHCID 15698228tert-Butyl N-cyclopropylcarbamate

Produkt 1

HCID 57941319N-nitroso-N-(tert-butoxycarbonyl)amino-cyclopropaneAusbeute 106,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
-30 °C

Versuchsvorschrift

Nitrosonium tetrafluoroborate (9.32 g, 79.8 mmol) was added carefully in several portions to a cooled (−30° C.) solution of N-(tert-butoxycarbonyl)cyclopropylamine (9.57 g, 60.9 mmol) and anhydrous pyridine (11.7 mL) in dry acetonitrile (150 mL). The solution was stirred at −30° C. for 30 minutes, and then at 0° C. for 2 hours. Ice water and EtOAc were added and the organic phase was separated and washed quickly with 1N HCl to remove pyridine. The organic phase was washed with 1N NaHCO3 and brine, dried (MgSO4), filtered, and evaporated under high vacuum with a water bath temperature below 40° C. to give N-nitroso-N-(tert-butoxycarbonyl)amino-cyclopropane (12.1 g, quantitative) as an oil.

Aufarbeitung

  1. waitat 0° C. for 2 hours
  2. customthe organic phase was separated
  3. washwashed quickly with 1N HCl
  4. customto remove pyridine
  5. washThe organic phase was washed with 1N NaHCO3 and brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated under high vacuum with a water bath temperature below 40° C.

Quellen und Nachweise

ORD-Eintrag
ord-aab3b91cf6294126a849440ff6925f04
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728029B2

Verknüpfte Notizen

Wird geladen…