Benzophenone imine → (4R,9aR)-6-(Benzhydrylidene-amino)-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester

HRID 11930

Reaktionsgleichung

Reaktionsgleichung von HRID 11930
[C:1]([O:5][C:6]([N:8]1[CH2:20][C@@H:19]([CH3:21])[N:18]2[C@H:10]([CH2:11][C:12]3[C:17]2=[N:16][C:15](Br)=[CH:14][CH:13]=3)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:23](=[NH:36])([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.CC(C)([O-])C.[Na+].C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:20][C@@H:19]([CH3:21])[N:18]2[C@H:10]([CH2:11][C:12]3[C:17]2=[N:16][C:15]([N:36]=[C:23]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:14][CH:13]=3)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 136809Benzophenone imineHCID 516892Sodium BicarbonateHCID 23676156Sodium t-butoxideHCID 86590113(4R,9aR)-6-bromo-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester

Produkt 1

HCID 86760227(4R,9aR)-6-(Benzhydrylidene-amino)-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl esterAusbeute 94,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture consisting of 0.20 g (0.54 mmol) (4R,9aR)-6-bromo-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester, 91 μl (0.54 mmol) benzophenone imine, 73.0 mg (0.76 mmol) sodium tert-butoxide, 5.6 mg (0.01 mmol) tris(dibenzylideneacetone)dipalladium chloroform complex and 10.1 mg (0.02 mmol) R-(+)-2,2′-bis(diphenylphosphino)-1,1′-binaphthalene in 3 ml toluene was stirred at reflux for 1 h. The reaction mixture was cooled to room temperature, poured into 10% aqueous sodium bicarbonate solution and extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and evaporated. The residue was purified by chromatography on silica gel (0.032–0.063 mm) with n-hexane:ethyl acetate (2:1) as eluant to afford the product as a yellow foam (94.3%).

Aufarbeitung

  1. temperatureat reflux for 1 h
  2. extractionextracted twice with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by chromatography on silica gel (0.032–0.063 mm) with n-hexane:ethyl acetate (2:1) as eluant

Quellen und Nachweise

ORD-Eintrag
ord-89d931138c0b4e07bc6f2a3eb238b96d
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07098337B2

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