2,2,2-Trichloroethyl chloroformate → racemic 3-(4-Chloro-phenyl)-8-aza-bicyclo[3.2.1]oct-2-ene-8-carboxylic acid 2,2,2-trichloro-ethyl ester

HRID 1266996

Reaktionsgleichung

Reaktionsgleichung von HRID 1266996
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:14][CH:13]3[N:15](C)[CH:10]([CH2:11][CH2:12]3)[CH:9]=2)=[CH:4][CH:3]=1.Cl[C:18]([O:20][CH2:21][C:22]([Cl:25])([Cl:24])[Cl:23])=[O:19]>ClC(Cl)(Cl)C>[Cl:23][C:22]([Cl:25])([Cl:24])[CH2:21][O:20][C:18]([N:15]1[CH:10]2[CH2:11][CH2:12][CH:13]1[CH:14]=[C:8]([C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)[CH2:9]2)=[O:19]

Komponenten

4

Edukt 2

HCID 870632,2,2-Trichloroethyl chloroformateHCID 4345323-(4-Chlorophenyl)-8-methyl-8-azabicyclo[3.2.1]oct-2-ene

Produkt 1

HCID 69707808racemic 3-(4-Chloro-phenyl)-8-aza-bicyclo[3.2.1]oct-2-ene-8-carboxylic acid 2,2,2-trichloro-ethyl esterAusbeute 92,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 62781,1,1-TrichloroethaneLösungsmittel

Versuchsvorschrift

Racemic 3-(4-Chloro-phenyl)-8-methyl-8-aza-bicyclo[3.2.1]oct-2-ene (4.98 g, 21.31 mmol) in 1,1,1-trichloroethane (60 mL) was heated at reflux and 2,2,2-trichloroethyl chloroformate (3.23 mL, 23.44 mmol) was added dropwise over 10 minutes. The reaction was refluxed for 3 hours, cooled and concentrated to a clear oil. Silica gel flash chromatography using 5% methanol/chloroform as the eluent yielded racemic 3-(4-Chloro-phenyl)-8-aza-bicyclo[3.2.1]oct-2-ene-8-carboxylic acid 2,2,2-trichloro-ethyl ester (7.77 g, 92.2%) as a clear oil which had the following properties: 1H NMR CDCl3 δ: 7.25 (s, 4H), 6.41 (m, 1H), 4.85 (m, 1H), 4.73 (s, 1H), 4.68-4.76 (m, 2H), 3.12 (d, J=17 Hz, 1H), 2.25 (m, 2H), 2.03 (m, 2H), 1.75 (m, 1H).

Aufarbeitung

  1. temperatureat reflux
  2. temperatureThe reaction was refluxed for 3 hours
  3. temperaturecooled
  4. concentrationconcentrated to a clear oil

Quellen und Nachweise

ORD-Eintrag
ord-a5a4808960b040f88a341db300eec28f
Quelldatensatz
uspto-grants-2003_04
Patentnummer
US06552015B2

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