Trichloroacetyl chloride → tert-Butyl 5,5-dichloro-6-oxo-2-azaspiro[3.3]heptane-2-carboxylate

HRID 1943595Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1943595
[CH2:1]=[C:2]1[CH2:5][N:4]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:3]1.[Cl:13][C:14]([Cl:19])(Cl)[C:15](Cl)=[O:16].COCCOC>C(OCC)C.[Zn]>[Cl:13][C:14]1([Cl:19])[C:15](=[O:16])[CH2:1][C:2]21[CH2:3][N:4]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:5]2

Komponenten

6

Edukt 3

HCID 6420Trichloroacetyl chlorideHCID 80711,2-DimethoxyethaneHCID 55269097tert-Butyl 3-methylideneazetidine-1-carboxylate

Produkt 1

HCID 69669942tert-Butyl 5,5-dichloro-6-oxo-2-azaspiro[3.3]heptane-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
10 °C

Versuchsvorschrift

Under an inert atmosphere, 7.728 g (118.19 mmoles) of zinc in nanopowder form are suspended in 100 ml of diethyl ether. 5.00 g (29.55 mmoles) of tert-butyl 3-methylene-azetidine-1-carboxylate (WO 2008124085) are added, then the medium is cooled to 10° C. A solution of 6.60 ml (59.09 mmoles) of trichloroacetyl chloride in ml of 1,2-dimethoxyethane is added drop by drop while maintaining the temperature of the reaction medium between 26 and 30° C. After stirring for 14 hrs at ambient temperature, the medium is filtered over celite, the celite is copiously rinsed with diethyl ether and the filtrate is partially concentrated under reduced pressure. The crude reaction product thus obtained is used as such in the following stage.

Aufarbeitung

  1. temperaturewhile maintaining the temperature of the reaction medium between 26 and 30° C
  2. filtrationthe medium is filtered over celite
  3. washthe celite is copiously rinsed with diethyl ether
  4. concentrationthe filtrate is partially concentrated under reduced pressure
  5. customThe crude reaction product
  6. customthus obtained

Quellen und Nachweise

ORD-Eintrag
ord-ade1e48e085e4c8d910f142994fe43b5
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08394787B2

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