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Binap, (A+-)- → HCID 66700958, Verbindung

HRID 1253700
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1253700
[CH2:1]1[C:5]2([CH2:10][CH2:9][NH:8][CH2:7][CH2:6]2)[CH2:4][CH2:3][N:2]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].Br[C:19]1[C:28]2[C:23](=[C:24]([C:29]([F:32])([F:31])[F:30])[CH:25]=[CH:26][CH:27]=2)[N:22]=[CH:21][CH:20]=1.CC([O-])(C)C.[Na+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[F:32][C:29]([F:30])([F:31])[C:24]1[CH:25]=[CH:26][CH:27]=[C:28]2[C:23]=1[N:22]=[CH:21][CH:20]=[C:19]2[N:8]1[CH2:7][CH2:6][C:5]2([CH2:1][N:2]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:3][CH2:4]2)[CH2:10][CH2:9]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 634876Binap, (A+-)-HCID 212773694-Bromo-8-(trifluoromethyl)quinolineHCID 23676156Sodium t-butoxideHCID 34178604tert-Butyl 2,8-diazaspiro[4.5]decane-2-carboxylate

Produkt 1

HCID 66700958HCID 66700958, VerbindungAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysator
HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of tert-butyl 2,8-diazaspiro[4.5]decane-2-carboxylate (2.5 mmol, 1.0 eq.) and 4-bromo-8-(trifluoromethyl)quinoline (2.5 mmol, 1.0 eq.) and tBuONa (7.5 mmol, 3.0 eq.) in toluene (12 ml) was degassed with argon for 10 min. BINAP (0.15 mmol, 0.06 eq.) and Pd(OAc)2 (0.05 mmol, 0.02 eq.) were added and the reaction mixture obtained was heated under reflux for 14 h. The reaction mixture was filtered over Celite and the filtrate was concentrated in vacuo in order to obtain the crude product, which was purified by column chromatography (silica gel, 22-25% ethyl acetate in hexane), in order to obtain the desired product. Yield: 40%

Aufarbeitung

  1. customwas degassed with argon for 10 min
  2. customthe reaction mixture obtained
  3. temperaturewas heated
  4. temperatureunder reflux for 14 h
  5. filtrationThe reaction mixture was filtered over Celite
  6. concentrationthe filtrate was concentrated in vacuo in order
  7. customto obtain the crude product, which
  8. customwas purified by column chromatography (silica gel, 22-25% ethyl acetate in hexane), in order

Quellen und Nachweise

ORD-Eintrag
ord-9601748f395e441dbd3c80c3e9a2a858
Quelldatensatz
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08455475B2

Notizen zur Reaktion

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