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Triphenylphosphine → HCID 67067087, Verbindung

HRID 2074329
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2074329
N(C(OCC)=O)=NC(OCC)=O.[OH:13][C:14]1[CH:35]=[CH:34][C:17]([O:18][CH:19]2[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]3[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=3)=[O:26])[CH2:21][CH2:20]2)=[CH:16][CH:15]=1.[Cl:36][C:37]1[CH:38]=[C:39]([CH:42]=[CH:43][CH:44]=1)[CH2:40]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)(Cl)Cl.C1COCC1>[ClH:36].[Cl:36][C:37]1[CH:38]=[C:39]([CH:42]=[CH:43][CH:44]=1)[CH2:40][O:13][C:14]1[CH:35]=[CH:34][C:17]([O:18][CH:19]2[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]3[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=3)=[O:26])[CH2:21][CH2:20]2)=[CH:16][CH:15]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 11776TriphenylphosphineHCID 701173-Chlorobenzyl alcoholHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 670670763-Pyridyl 4-(4-hydroxyphenoxy)-1-piperidinecarboxylate

Produkt 1

HCID 67067087HCID 67067087, VerbindungAusbeute 24,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212
Chloroform
Lösungsmittel
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Diethyl azodicarboxylate (0.35 ml, 40% Tol solution) was dropwise added to a THF (5 ml) solution containing 3-pyridyl 4-(4-hydroxyphenoxy)-1-piperidinecarboxylate (160 mg), 3-chlorobenzyl alcohol (110 mg) and triphenylphosphine (200 mg) at 0° C., followed by stirring at room temperature for 24 hours. The reaction solution was diluted with chloroform, washed with aqueous saturated sodium hydrogencarbonate solution, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: hexane:EtOAc=1:3 (v/v)). The resulting oil was dissolved in EtOAc (5 ml), and 4 M hydrogen chloride/EtOAc solution (1 ml) was added thereto, followed by stirring at room temperature. The solvent was evaporated under reduced pressure, and the precipitated solid was recrystallized from EtOAc/2-propanol to obtain 3-pyridyl 4-{4-[(3-chlorobenzyl)oxy]phenoxy}-1-piperidinecarboxylate hydrochloride (45 mg).

Aufarbeitung

  1. washwashed with aqueous saturated sodium hydrogencarbonate solution
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (eluent: hexane:EtOAc=1:3 (v/v))
  5. dissolutionThe resulting oil was dissolved in EtOAc (5 ml)
  6. addition4 M hydrogen chloride/EtOAc solution (1 ml) was added
  7. stirringby stirring at room temperature
  8. customThe solvent was evaporated under reduced pressure
  9. customthe precipitated solid was recrystallized from EtOAc/2-propanol

Quellen und Nachweise

ORD-Eintrag
ord-c8ef446a4d694b59ab0d9068fd805279
Quelldatensatz
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07919495B2

Notizen zur Reaktion

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