Nitric Acid → 1-((1R,5S,6R)-6-(4-nitro-phenyl)-3-aza-bicyclo[3.2.0]hept-3-yl)-propan-1-one
Reaction equation
[C:1]1([C@@H:7]2[CH2:13][C@@H:12]3[C@H:8]2[CH2:9][N:10]([C:14](=[O:17])[CH2:15][CH3:16])[CH2:11]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+:18]([O-])([OH:20])=[O:19].S(=O)(=O)(O)O>[N+](C)([O-])=O.O>[N+:18]([C:4]1[CH:3]=[CH:2][C:1]([C@@H:7]2[CH2:13][C@@H:12]3[C@H:8]2[CH2:9][N:10]([C:14](=[O:17])[CH2:15][CH3:16])[CH2:11]3)=[CH:6][CH:5]=1)([O-:20])=[O:19]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -8 °C
Procedure
1.0 g of 1-((1R,5S,6R)-6-Phenyl-3-aza-bicyclo[3.2.0]hept-3-yl)-propan-1-one (4.36 mmol) were dissolved in 12 ml of nitromethane. At −8° C., a mixture of 0.3 ml of nitric acid (65%, 4.36 mmol) and 4.6 ml of sulphuric acid (95%) in 0.76 ml of water were added dropwise within 45 minutes. Stirring at −8° C. was continued for 30 minutes, before 20 ml of ice water were added and the aqueous phase was extracted twice with diethyl ether, the combined organic layers were dried over magnesium sulfate, filtered, and the solvent was evaporated under reduced pressure to yield 1.27 g of the product as a mixture of 2:1 para versus ortho substituted product which was used without further separation.
Workup
- additionwere added dropwise within 45 minutes
- additionwere added
- extractionthe aqueous phase was extracted twice with diethyl ether
- dry with materialthe combined organic layers were dried over magnesium sulfate
- filtrationfiltered
- customthe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-7720f66765ac45a2af1becf64bacf3f4
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07834048B2
Reaction notes
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