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Triphenylphosphine → Tert-butyl 4-(2-(ethylthio)quinazolin-7-yloxy)piperidine-1-carboxylate

HRID 2079668
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2079668
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([O:24][C:25]([N:27]1[CH2:32][CH2:31][CH:30]([OH:33])[CH2:29][CH2:28]1)=[O:26])([CH3:23])([CH3:22])[CH3:21].[CH2:34]([S:36][C:37]1[N:46]=[CH:45][C:44]2[C:39](=[CH:40][C:41](O)=[CH:42][CH:43]=2)[N:38]=1)[CH3:35]>C1COCC1>[CH2:34]([S:36][C:37]1[N:46]=[CH:45][C:44]2[C:39](=[CH:40][C:41]([O:33][CH:30]3[CH2:31][CH2:32][N:27]([C:25]([O:24][C:20]([CH3:23])([CH3:21])[CH3:22])=[O:26])[CH2:28][CH2:29]3)=[CH:42][CH:43]=2)[N:38]=1)[CH3:35]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 11776TriphenylphosphineHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 1360299282-(Ethylthio)quinazolin-7-ol

Produkt 1

HCID 67101955Tert-butyl 4-(2-(ethylthio)quinazolin-7-yloxy)piperidine-1-carboxylateAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

To a solution of triphenylphosphine (2 eq) in THF was added di-terbutylazodicarboxylate (2 eq). The mixture was stirred 15 minutes at ambient temperature under nitrogen atmosphere. To that was added tert-butyl-4-hydroxypiperidine-1-carboxylate (5 eq). The mixture was stirred 15 minutes at ambient temperature followed by addition of 2-(ethylthio) quinazolin-7-ol (1 eq). The mixture was stirred overnight at ambient temperature. The reaction mixture was concentrated and purified by flash column chromatography (10% EtOAc/Hexane) to provide product as a white solid in 90% yield. ES/MS m/z 390.1 (MH+).

Aufarbeitung

  1. stirringThe mixture was stirred 15 minutes at ambient temperature
  2. stirringThe mixture was stirred overnight at ambient temperature
  3. concentrationThe reaction mixture was concentrated
  4. custompurified by flash column chromatography (10% EtOAc/Hexane)
  5. customto provide product as a white solid in 90% yield

Quellen und Nachweise

ORD-Eintrag
ord-ce4eee9a0cee4e84bfbff6469135e045
Quelldatensatz
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07932262B2

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