Nitric Acid → (4S)-4-((tert-butyl(dimethyl)silyl)oxy)-1-(1-methyl-4-nitro-1H-pyrazol-3-yl)pyrrolidin-2-one
Reaction equation
[Si:1]([O:8][C@@H:9]1[CH2:13][N:12]([C:14]2[CH:18]=[CH:17][N:16]([CH3:19])[N:15]=2)[C:11](=[O:20])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[N+:21]([O-])([OH:23])=[O:22].C(=O)([O-])O.[Na+]>C(OC(=O)C)(=O)C>[Si:1]([O:8][C@@H:9]1[CH2:13][N:12]([C:14]2[C:18]([N+:21]([O-:23])=[O:22])=[CH:17][N:16]([CH3:19])[N:15]=2)[C:11](=[O:20])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of (4S)-4-((tert-butyl(dimethyl)silyl)oxy)-1-(1-methyl-1H-pyrazol-3-yl)pyrrolidin-2-one (2.07 g) in acetic anhydride (21 mL) was added a solution of fuming nitric acid (0.58 mL) in acetic anhydride (21 mL), and the mixture was stirred under for 1.5 hr under ice-cooling. To the reaction mixture were added ice water and saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (1.9 g).
Workup
- temperaturecooling
- extractionthe mixture was extracted with ethyl acetate
- washThe extract was washed with saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- customthe solvent was evaporated under reduced pressure
- customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)
Sources & evidence
- ORD record
- ord-e3b1e987848f4ab6941f57384848f1a1
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09321757B2
Reaction notes
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