Acetic Acid → 6-(3-Bromophenyl)-10-{[4-(trifluoromethyl)phenyl]sulfonyl}-4,5,6,7,8,9-hexahydro-1H-4,8-epiminocycloocta[c]pyrazole

HRID 2061615Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2061615
O.[NH2:2][NH2:3].[Br:4][C:5]1[CH:6]=[C:7]([CH:11]2[CH2:18][CH:17]3[N:19]([S:20]([C:23]4[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=4)(=[O:22])=[O:21])[CH:13]([CH2:14][C:15](=O)[C:16]3=[CH:33]O)[CH2:12]2)[CH:8]=[CH:9][CH:10]=1.C(O)(=O)C>CCO>[Br:4][C:5]1[CH:6]=[C:7]([CH:11]2[CH2:12][CH:13]3[N:19]([S:20]([C:23]4[CH:28]=[CH:27][C:26]([C:29]([F:30])([F:31])[F:32])=[CH:25][CH:24]=4)(=[O:22])=[O:21])[CH:17]([C:16]4[CH:33]=[N:3][NH:2][C:15]=4[CH2:14]3)[CH2:18]2)[CH:8]=[CH:9][CH:10]=1

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 24654Hydrazine hydrate (1:1)HCID 673031627-(3-Bromophenyl)-2-(hydroxymethylene)-9-(4-(trifluoromethyl)phenylsulfonyl)-9-azabicyclo[3.3.1]nonan-3-one

Produkt 1

HCID 452798896-(3-Bromophenyl)-10-{[4-(trifluoromethyl)phenyl]sulfonyl}-4,5,6,7,8,9-hexahydro-1H-4,8-epiminocycloocta[c]pyrazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

21% NaOEt (6 ml, 16.1 mmol) was added to a solution of 7-(3-Bromophenyl)-9-(4-(trifluoromethyl)phenylsulfonyl)-9-azabicyclo[3.3.1]nonan-3-one (90) (2.28 g, 4.54 mmol) and ethyl formate (6 ml, 74.5 mmol) in THF (20 ml). The solution was placed into a preheated oil bath at 60° C. After stirring for 30 min, the solution was cooled to ambient temperature, diluted with saturated aqueous NH4Cl, and extracted with EtOAc. The combined organic extracts were dried over MgSO4, filtered, and concentrated to afford 7-(3-bromophenyl)-2-(hydroxymethylene)-9-(4-(trifluoromethyl)phenylsulfonyl)-9-azabicyclo[3.3.1]nonan-3-one. Hydrazine monohydrate (3 ml) was added to a solution of 7-(3-bromophenyl)-2-(hydroxymethylene)-9-(4-(trifluoromethyl)phenylsulfonyl)-9-azabicyclo[3.3.1]nonan-3-one and glacial acetic acid (1 ml) in EtOH (20 ml). After stirring for 18 h, the solution was concentrated to afford compound 92.

Aufarbeitung

  1. concentrationthe solution was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-2062d4a4e1cd4083b0133d6813e2817d
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08283358B2

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