Water → HCID 118061154, compound
Reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:11][CH2:10][CH2:9][C:8]2=[O:12])=[N:3]1.[Li+].[CH3:14][Si]([N-][Si](C)(C)C)(C)C.C1COCC1.IC.O>C1COCC1>[CH3:14][CH:9]1[CH2:10][CH2:11][N:7]([C:4]2[CH:5]=[CH:6][N:2]([CH3:1])[N:3]=2)[C:8]1=[O:12]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a solution of 1-(1-methyl-1H-pyrazol-3-yl)pyrrolidin-2-one (1.5 g) in THF (60 mL) was added 1.3 M LHMDS THF solution (7.3 mL) at −78° C., and the mixture was stirred at −78° C. for 1 hr. Iodomethane (0.60 mL) was added to the reaction mixture, and the mixture was stirred at room temperature for 4 hr. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium 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 (927 mg).
Workup
- stirringthe mixture was stirred at room temperature for 4 hr
- extractionthe mixture was extracted with ethyl acetate
- washThe extract was washed with saturated brine
- dry with materialdried over anhydrous sodium 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-1cd047b539294511bf443553bc8e3308
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09321757B2
Reaction notes
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