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Water → aziridin-1-yl(6,6-diphenyl-6,7-dihydro-1H-indazol-3-yl)methanone

HRID 1243825
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1243825
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[N:19]1([C:22]([C:24]2[C:32]3[CH:31]=[CH:30][C:29]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[CH2:28][C:27]=3[N:26](COCC[Si](C)(C)C)[N:25]=2)=[O:23])[CH2:21][CH2:20]1.O>O1CCCC1>[N:19]1([C:22]([C:24]2[C:32]3[CH:31]=[CH:30][C:29]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)([C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=4)[CH2:28][C:27]=3[NH:26][N:25]=2)=[O:23])[CH2:21][CH2:20]1
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Komponenten

5

Edukt 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 21928926aziridin-1-yl(6,6-diphenyl-1-(2-trimethylsilanylethoxymethyl)-6,7-dihydro-1H-indazol-3-yl)methanone

Produkt 1

HCID 21929654aziridin-1-yl(6,6-diphenyl-6,7-dihydro-1H-indazol-3-yl)methanoneAusbeute 470,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel
2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

6 cm3 of a commercial 1 M solution of tetrabutylammonium fluoride in tetrahydrofuran are added to a solution of 0.235 g of aziridin-1-yl(6,6-diphenyl-1-(2-trimethylsilanylethoxymethyl)-6,7-dihydro-1H-indazol-3-yl)methanone in 2.5 cm3 of tetrahydrofuran cooled to a temperature in the region of 0° C. After stirring for about 48 hours at a temperature in the region of 20° C., the mixture is poured into 30 cm3 of an ice plus water mixture and extracted with three times 50 cm3 of diethyl ether. The combined organic phases are washed with three times 25 cm3 of water and 25 cm3 of saturated aqueous sodium chloride solution, dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (13 kPa). After flash chromatography on a column of silica [eluent: dichloromethane/methanol (90/10 by volume)], 0.80 g of aziridin-1-yl(6,6-diphenyl-6,7-dihydro-1H-indazol-3-yl)methanone is thus obtained in the form of a solid, the characteristics of which are as follows:

Aufarbeitung

  1. extractionextracted with three times 50 cm3 of diethyl ether
  2. washThe combined organic phases are washed with three times 25 cm3 of water and 25 cm3 of saturated aqueous sodium chloride solution
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under reduced pressure (13 kPa)

Quellen und Nachweise

ORD-Eintrag
ord-87a4a3b99e1345a49f7de4409dedd799
Quelldatensatz
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07119115B2

Notizen zur Reaktion

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