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Tert-butyl 4-hydroxypiperidine-1-carboxylate → HCID 49759211, Verbindung

HRID 1879643
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1879643
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.CC(C)([O-])C.[K+].F[C:22]1[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[C:24]([O:31][CH3:32])[CH:23]=1>O1CCCC1>[CH3:32][O:31][C:24]1[CH:23]=[C:22]([CH:27]=[CH:26][C:25]=1[N+:28]([O-:30])=[O:29])[O:1][CH:2]1[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 27792505-Fluoro-2-nitroanisoleHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 49759211HCID 49759211, VerbindungAusbeute 43,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a mixture of tert-butyl 4-hydroxypiperidine-1-carboxylate (1.49 g) and tetrahydrofuran (30 mL), potassium tert-butoxide (830 mg) was added under ice cooling and stirred for 30 minutes, followed by addition of a mixture of 4-fluoro-2-methoxy-1-nitrobenzene (1.00 g) and tetrahydrofuran (20 mL). After stirring at room temperature for 3 hours, the reaction mixture was extracted by addition of water and ethyl acetate, washed with saturated aqueous sodium chloride, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (eluent; n-hexane:diethyl ether=4:1) to give tert-butyl 4-(3-methoxy-4-nitrophenoxy)piperidine-1-carboxylate (898 mg).

Aufarbeitung

  1. additionwas added under ice cooling
  2. stirringAfter stirring at room temperature for 3 hours
  3. extractionthe reaction mixture was extracted by addition of water and ethyl acetate
  4. washwashed with saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (eluent; n-hexane:diethyl ether=4:1)

Quellen und Nachweise

ORD-Eintrag
ord-81bd906ac1ce4334a3d0cb42c221f60c
Quelldatensatz
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08318702B2

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