Acetic Acid → 6-(3-Bromophenyl)-10-{[4-(trifluoromethyl)phenyl]sulfonyl}-4,5,6,7,8,9-hexahydro-1H-4,8-epiminocycloocta[c]pyrazole
Reaction equation
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]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
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.
Workup
- concentrationthe solution was concentrated
Sources & evidence
- ORD record
- ord-2062d4a4e1cd4083b0133d6813e2817d
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08283358B2
Reaction notes
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