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(Trimethylsilyl)acetonitrile → (Z)-1-(t-Butoxycarbonyl)-4-(t-butyldimethylsilyloxy)-3-(cyanomethylidene)piperidine

HRID 1171758
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1171758
C[Si]([CH2:5][C:6]#[N:7])(C)C.C([N-]C(C)C)(C)C.[Li+].[C:16]([O:20][C:21]([N:23]1[CH2:28][CH2:27][CH:26]([O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])[C:25](=O)[CH2:24]1)=[O:22])([CH3:19])([CH3:18])[CH3:17]>O1CCCC1>[C:16]([O:20][C:21]([N:23]1[CH2:28][CH2:27][CH:26]([O:29][Si:30]([C:33]([CH3:36])([CH3:34])[CH3:35])([CH3:31])[CH3:32])/[C:25](=[CH:5]\[C:6]#[N:7])/[CH2:24]1)=[O:22])([CH3:18])([CH3:17])[CH3:19]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 87557(Trimethylsilyl)acetonitrileHCID 2724682Lithium diisopropylamideHCID 231387171-(t-Butoxycarbonyl)-4-(t-butyldimethylsilyloxy)piperidin-3-one

Produkt 1

HCID 68764725(Z)-1-(t-Butoxycarbonyl)-4-(t-butyldimethylsilyloxy)-3-(cyanomethylidene)piperidineAusbeute 27 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel
2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of trimethylsilylacetonitrile (1.3 ml) in tetrahydrofuran (THF) (30 ml) was added at −78° C. lithium diisopropylamide (2.0 M in hexane, 4.7 ml). The resulting mixture was stirred at −78° C. for 0.5 hours, and then a solution of 1-(t-butoxycarbonyl)-4-(t-butyldimethylsilyloxy)piperidin-3-one (3 g) in THF (10 ml) was added at the same temperature. The resulting mixture was stirred for one hour while the temperature was raised to room temperature. The mixture was concentrated in vacuo, and the residue was purified by chromatography on silica gel using a mixture of hexane and ethyl acetate (9:1) as the eluent to afford the title compound (880 mg, yield: 27%) as the less polar isomer as a yellow oil.

Aufarbeitung

  1. stirringThe resulting mixture was stirred for one hour while the temperature
  2. temperaturewas raised to room temperature
  3. concentrationThe mixture was concentrated in vacuo
  4. customthe residue was purified by chromatography on silica gel using
  5. additiona mixture of hexane and ethyl acetate (9:1) as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-1dc922227a074c8992803e6e194ea0f5
Quelldatensatz
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07829580B2

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