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Triphenylphosphine → HCID 54565828, Verbindung

HRID 617298
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 617298
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[C:32]([O:36][C:37]([N:39]1[CH2:43][CH2:42][CH2:41][C@H:40]1[CH2:44][OH:45])=[O:38])([CH3:35])([CH3:34])[CH3:33].[CH3:46][C:47]1[N:52]=[CH:51][C:50](O)=[CH:49][CH:48]=1>C1COCC1>[CH3:46][C:47]1[N:52]=[CH:51][C:50]([O:45][CH2:44][C@@H:40]2[CH2:41][CH2:42][CH2:43][N:39]2[C:37]([O:36][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:38])=[CH:49][CH:48]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 142752-Methyl-5-hydroxypyridineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 643448(S)-(-)-N-Boc-prolinol

Produkt 1

HCID 54565828HCID 54565828, VerbindungAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of triphenylphosphine (3.83 g, 14.60 mmol) in 40 mL of anhydrous THF at 0° C. was added diethyl azodicarboxylate (2.3 mL, 14.60 mmol) dropwise. The mixture was stirred at 0° C. for 30 minutes, then brought to room temperature. (S)-1-t-Butoxycarbonyl-2-pyrrolidinemethanol (1.96 g, 9.75 mmol, Aldrich Chemical Co.) and 6-methyl-3-pyridinol (Aldrich Chemical Co., 1.60 g, 14.60 mmol) were added to the reaction vessel, and the mixture was stirred for 16 hours. Solvent was removed in vacuo, and the residue was diluted with hexane and sonicated for 30 minutes. The resulting precipitate was filtered and washed with hexane. The hexane was removed in vacuo. The residue was purified by silica gel flash chromatography using a gradient from 100% hexane to a 1:1 solution of ethyl acetatelh exane (100%Hex, 10% EtOAc/Hex, 20%EtOAc/Hex, 1:1EtOAc/Hex) to give 1.61 g (57% ) of the title compound as a pale yellow oil. TLC Rf=0.42 (1:1 EtOAc/Hex). MS (DCI/NH3) m/e: 293 (M+H)+.

Aufarbeitung

  1. custombrought to room temperature
  2. stirringthe mixture was stirred for 16 hours
  3. customSolvent was removed in vacuo
  4. additionthe residue was diluted with hexane
  5. customsonicated for 30 minutes
  6. filtrationThe resulting precipitate was filtered
  7. washwashed with hexane
  8. customThe hexane was removed in vacuo
  9. customThe residue was purified by silica gel flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-64094540a9764c61ab4f91352af4ff59
Quelldatensatz
uspto-grants-1999_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05948793

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