Methanesulfonic Acid → Ethyl 2-oxo-1-azacyclodecane-10-carboxylate

HRID 5390

Reaktionsgleichung

Reaktionsgleichung von HRID 5390
[CH2:1]([O:3][C:4]([CH:6]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][C:7]1=[O:15])=[O:5])[CH3:2].CS(O)(=O)=O.[N-:21]=[N+]=[N-].[Na+].[OH-].[NH4+]>C(Cl)(Cl)Cl>[O:15]=[C:7]1[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[NH:21]1

Komponenten

6

Edukt 4

HCID 6395Methanesulfonic AcidHCID 14923Ammonium HydroxideHCID 33557Sodium AzideHCID 107210Ethyl 2-oxocyclononanecarboxylate

Produkt 1

HCID 19930826Ethyl 2-oxo-1-azacyclodecane-10-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

2-Ethoxycarbonyl-cyclononanone (13.72 g, 64.7 mmol) is dissolved in chloroform (200 mL) and cooled to 0° C. Methanesulfonic acid (62.4 g, 650 mmol) is added, followed by sodium azide (12.68 g, 195 mmol). The reaction is stirred at room temperature for 30 minutes, and then heated to reflux for 4 hours. The reaction mixture is poured onto ice, made basic with concentrated ammonium hydroxide (pH=9), and extracted several times with methylene chloride. The combined organic layers are dried (MgSO4), and the solvent is evaporated. The product is purified by silica gel chromatography (40% ethyl acetate/hexane) to give ethyl 2-oxo-1-azacyclodecane-10-carboxylate, m.p. 101°-103° C.

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux for 4 hours
  3. additionThe reaction mixture is poured onto ice
  4. extractionextracted several times with methylene chloride
  5. dry with materialThe combined organic layers are dried (MgSO4)
  6. customthe solvent is evaporated
  7. customThe product is purified by silica gel chromatography (40% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-457a83af2b8e486aa8de7028583f3486
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05244889

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