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Tetrahydrofuran → (+)-(4aR)-(10bR)-4-methyl-8-(5-quinolinyl)-10b-methyl-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one

HRID 1682903
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1682903
Br[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[C:12](=[O:15])([O-])[O-].[Na+].[Na+].[CH2:18]1[CH2:22]O[CH2:20][CH2:19]1>C(OCC)(=O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:8][N:7]1[C@H:6]2[C@@:18]([CH3:22])([C:18]3[CH:22]=[CH:11][C:2]([C:2]4[CH:11]=[CH:10][CH:9]=[C:8]5[C:3]=4[CH:4]=[CH:5][CH:6]=[N:7]5)=[CH:3][C:19]=3[CH2:20][CH2:5]2)[CH2:19][CH2:20][C:12]1=[O:15]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 8028TetrahydrofuranHCID 10340Sodium CarbonateHCID 8173215-Bromoquinoline

Produkt 1

HCID 53902869(+)-(4aR)-(10bR)-4-methyl-8-(5-quinolinyl)-10b-methyl-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-oneAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11979704
Tetrakis(triphenylphosphine)palladium
Katalysator
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A 15 mL round bottom flask was charged with (+)-(4aR)-(10bR)-4-methyl-10b-methyl-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one-8-boronic acid (178 mg, 0.65 mmol), tetrakis(triphenylphosphine) palladium (0) (23 mg, 0.02 mmol), 5-bromoquinoline (135 mg, 0.65 mmol), 0.65 mL of 2M sodium carbonate and 2 mL of THF, fitted with a reflux condenser, and the stirred mixture was heated at 80°, under nitrogen, for 24 h. The mixture was cooled, diluted with ethyl acetate (75 mL) and washed with brine (2×25 mL). The combined organic extracts were dried over sodium sulfate, concentrated, and purified by silica gel chromatography (ethyl acetate eluent) to give 128 mg (55%) of the title compound as an amorphous foam. mp 100°-104°. FDMS: m/e=356. α[D]589 =+61.77 (c=0.35, chloroform).

Aufarbeitung

  1. customfitted with a reflux condenser
  2. temperaturethe stirred mixture was heated at 80°, under nitrogen, for 24 h
  3. temperatureThe mixture was cooled
  4. washwashed with brine (2×25 mL)
  5. dry with materialThe combined organic extracts were dried over sodium sulfate
  6. concentrationconcentrated
  7. custompurified by silica gel chromatography (ethyl acetate eluent)

Quellen und Nachweise

ORD-Eintrag
ord-2896e94de0fb468f8484a93792844c06
Quelldatensatz
uspto-grants-1997_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05635197

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