Nitric Acid → HCID 121317102, compound
Reaction equation
[F:1][CH:2]([F:19])[C@:3]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])[NH:8][C:7](=[O:9])[CH2:6][CH2:5][C:4]1([F:11])[F:10].OS(O)(=O)=O.[N+:25]([O-])([OH:27])=[O:26].[OH-].[Na+]>FC(F)(F)C(O)=O>[F:19][CH:2]([F:1])[C@:3]1([C:12]2[CH:17]=[C:16]([N+:25]([O-:27])=[O:26])[CH:15]=[CH:14][C:13]=2[F:18])[NH:8][C:7](=[O:9])[CH2:6][CH2:5][C:4]1([F:11])[F:10]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
(S)-6-(difluoromethyl)-5,5-difluoro-6-(2-fluorophenyl)piperidin-2-one (880 mg, 3.15 mmol) was suspended in trifluoroacetic acid (2.55 mL). The mixture was cooled to 0° C. and concentrated H2SO4 (2.46 g, 24.3 mmol) was added. Then, HNO3 (661.61 mg, 6.30 mmol) was added dropwise. After 2 hours of stirring at 25° C., the reaction mixture was poured onto 100 g ice and basified to pH>11 using 5 M NaOH (aq). The suspension was extracted with ethyl acetate (150 mL). The phases were separated and the aqueous layer was extracted with ethyl acetate (2×70 mL). The combined organic phases were washed with a solution of saturated aqueous NH4Cl (30 mL) and water (30 mL), dried over MgSO4, filtered, and concentrated under reduced pressure to afford (S)-6-(difluoromethyl)-5,5-difluoro-6-(2-fluoro-5-nitrophenyl)piperidin-2-one (1.00 g, crude).
Workup
- extractionThe suspension was extracted with ethyl acetate (150 mL)
- customThe phases were separated
- extractionthe aqueous layer was extracted with ethyl acetate (2×70 mL)
- washThe combined organic phases were washed with a solution of saturated aqueous NH4Cl (30 mL) and water (30 mL)
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-c887e2ef5a9f4bdd9ac0b0e8833bef6e
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09346797B1
Reaction notes
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