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Ethyl 2,3-di-oxo-1-azacyclodecane-10-carboxylate → Ethyl 3-(trimethylsilylmethyl)-3-hydroxy-2-oxo-1-azacyclodecane-10-carboxylate

HRID 21965
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 21965
[O:1]=[C:2]1[C:11](=[O:12])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH:4]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[NH:3]1.[CH3:18][Si:19]([CH2:22][Mg]Cl)([CH3:21])[CH3:20]>CCOCC>[CH3:18][Si:19]([CH2:22][C:11]1([OH:12])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH:4]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[NH:3][C:2]1=[O:1])([CH3:21])[CH3:20]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 19930804Ethyl 2,3-di-oxo-1-azacyclodecane-10-carboxylateHCID 178418680HCID 178418680, Verbindung

Produkt 1

HCID 19930812Ethyl 3-(trimethylsilylmethyl)-3-hydroxy-2-oxo-1-azacyclodecane-10-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Ethyl 2,3-di-oxo-1-azacyclodecane-10-carboxylate (5.02 g, 20.81 mmol) is dissolved in ether (50 mL), and cooled to 0° C. Trimethylsilylmethylmagnesium chloride (42.0 mL of a 1.0M solution in ether, 42.0 mmol) is added dropwise, the reaction is stirred at 0° C. for 20 minutes, and then heated to reflux overnight. The reaction is quenched with saturated ammonium chloride, and extracted several times with ethyl acetate. The combined organic layers are dried (Na2SO4), and the solvent is evaporated. The product is purified by silica gel chromatography (10% ethyl acetate/hexane) to give separately the two diastereomers of ethyl 3-(trimethylsilylmethyl)-3-hydroxy-2-oxo-1-azacyclodecane-10-carboxylate; major isomer, m.p. 129°-130° C.; minor isomer, m.p. 175°-177° C.

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux overnight
  3. customThe reaction is quenched with saturated ammonium chloride
  4. extractionextracted several times with ethyl acetate
  5. dry with materialThe combined organic layers are dried (Na2SO4)
  6. customthe solvent is evaporated
  7. customThe product is purified by silica gel chromatography (10% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-a31e8b575c884584a0ca2bedb89b6bf4
Quelldatensatz
uspto-grants-1995_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05426103

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