Ethyl formate → 7-(3-Bromophenyl)-2-(hydroxymethylene)-9-(4-(trifluoromethyl)phenylsulfonyl)-9-azabicyclo[3.3.1]nonan-3-one

HRID 2061614Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2061614
[CH3:1][CH2:2][O-:3].[Na+].[Br:5][C:6]1[CH:7]=[C:8]([CH:12]2[CH2:19][CH:18]3[N:20]([S:21]([C:24]4[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=4)(=[O:23])=[O:22])[CH:14](C[C:16](=[O:34])[CH2:17]3)[CH2:13]2)[CH:9]=[CH:10][CH:11]=1.C(OCC)=O>C1COCC1.[NH4+].[Cl-]>[Br:5][C:6]1[CH:7]=[C:8]([CH:12]2[CH2:13][CH:14]3[N:20]([S:21]([C:24]4[CH:25]=[CH:26][C:27]([C:30]([F:32])([F:33])[F:31])=[CH:28][CH:29]=4)(=[O:23])=[O:22])[CH:18]([CH2:17][C:16](=[O:34])[C:1]3=[CH:2][OH:3])[CH2:19]2)[CH:9]=[CH:10][CH:11]=1

Komponenten

6

Edukt 3

HCID 8025Ethyl formateHCID 2723922Sodium ethoxideHCID 673032167-(3-Bromophenyl)-9-(4-(trifluoromethyl)phenylsulfonyl)-9-azabicyclo[3.3.1]nonan-3-one

Produkt 1

HCID 673031627-(3-Bromophenyl)-2-(hydroxymethylene)-9-(4-(trifluoromethyl)phenylsulfonyl)-9-azabicyclo[3.3.1]nonan-3-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 25517Ammonium ChlorideLösungsmittel

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. customThe solution was placed into a preheated oil bath at 60° C
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-af228f87e7af4796ab62ba7b5be9323f
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08283358B2

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