Triethylamine → HCID 89557130, Verbindung

HRID 870480Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 870480
C([O:8][C:9]([Cl:12])(Cl)Cl)(OC(Cl)(Cl)Cl)=O.[Si:13]([O:20][CH:21]1[CH2:24][NH:23][CH2:22]1)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14].C(N(CC)CC)C>ClCCl>[Si:13]([O:20][CH:21]1[CH2:24][N:23]([C:9]([Cl:12])=[O:8])[CH2:22]1)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 574386563-((tert-Butyldimethylsilanyl)oxy)azetidine

Produkt 1

HCID 89557130HCID 89557130, VerbindungAusbeute 97,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of ditrichloromethyl carbonate (2.38 g, 8.02 mmol, 1.50 equiv) in dichloromethane (20 mL) was added a solution of 3-[(tert-butyldimethylsilyl)oxy]azetidine (1 g, 5.34 mmol, 1.00 equiv) in dichloromethane (5 mL) dropwise with stirring at 0° C. over 30 min. Stirring was continued for 30 min whereupon a solution of triethylamine (810 mg, 8.00 mmol, 1.50 equiv) in dichloromethane (5 mL) was added dropwise with stirring at 0° C. in 30 min. The resulting solution was stirred overnight at room temperature. The reaction was then quenched by the addition of 20 mL of sodium bicarbonate (sat.). The resulting solution was extracted with 3×20 mL of ethyl acetate and the organic layers combined, washed with 2×40 mL of sodium chloride (sat.), dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:15). Purification afforded 1.3 g (97%) of 3-[(tert-butyldimethylsilyl)oxy]azetidine-1-carbonyl chloride as a light yellow liquid.

Aufarbeitung

  1. stirringStirring
  2. additionwas added dropwise
  3. stirringwith stirring at 0° C. in 30 min
  4. stirringThe resulting solution was stirred overnight at room temperature
  5. customThe reaction was then quenched by the addition of 20 mL of sodium bicarbonate (sat.)
  6. extractionThe resulting solution was extracted with 3×20 mL of ethyl acetate
  7. washwashed with 2×40 mL of sodium chloride (sat.)
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated under vacuum
  10. customPurification

Quellen und Nachweise

ORD-Eintrag
ord-8afdd8e12a614e848464224f5bac4f46
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08969557B2

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