Boron trifluoride etherate → Ethyl 3-methylidene-2-oxo-1-azacyclodecane-10-carboxylate

HRID 21966

Reaktionsgleichung

Reaktionsgleichung von HRID 21966
C[Si]([CH2:5][C:6]1(O)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH:9]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[NH:8][C:7]1=[O:21])(C)C.B(F)(F)F.CCOCC>C(Cl)Cl>[CH2:5]=[C:6]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH:9]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[NH:8][C:7]1=[O:21]

Komponenten

4

Edukt 2

HCID 8000Boron trifluoride etherateHCID 19930812Ethyl 3-(trimethylsilylmethyl)-3-hydroxy-2-oxo-1-azacyclodecane-10-carboxylate

Produkt 1

HCID 19930803Ethyl 3-methylidene-2-oxo-1-azacyclodecane-10-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Ethyl 3-(trimethylsilylmethyl)-3-hydroxy-2-oxo-1-azacyclodecane-10-carboxylate (0.98 g, 2.98 mmol) is dissolved in methylene chloride (50 mL), and boron trifluoride etherate (1.8 mL, 15 mmol) is added. The reaction is stirred at room temperature for 26 hours. The reaction is then quenched with saturated ammonium chloride 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 (20% ethyl acetate/hexane) to give ethyl 3-methylidene-2-oxo-1-azacyclodecane-10-carboxylate, m.p. 91°-92° C.

Aufarbeitung

  1. customThe reaction is then quenched with saturated ammonium chloride
  2. extractionextracted several times with methylene chloride
  3. dry with materialThe combined organic layers are dried (MgSO4)
  4. customthe solvent is evaporated
  5. customThe product is purified by silica gel chromatography (20% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-bc023ee232b849a4ba76f663d1c2ba20
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05426103

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