Trifluoroacetic acid → 2-(1-Benzyl-pyrrolidin-3-yl)-5-nitro-pyridine
Reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH:10]=[CH2:11])=[N:8][CH:9]=1)([O-:3])=[O:2].FC(F)(F)C(O)=O.[CH2:19]([N:26]([CH2:32]OC)[CH2:27][Si](C)(C)C)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>ClCCl>[CH2:19]([N:26]1[CH2:32][CH2:11][CH:10]([C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][N:8]=2)[CH2:27]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1Participants
5
Procedure
0.15 g of 5-nitro-2-vinyl-pyridine were dissolved in 2.5 ml of dichloromethane, 0.149 g of trifluoroacetic acid (1.31 mmol) were added, followed by slow addition of 0.928 g of N-benzyl-N-(methoxymethyl)-N-trimethylsilylmethylamine (3.91 mmol). Stirring was continued at room temperature for 1 h, before the reaction mixture was washed with aqueous sodium hydrogencarbonate, the aqueous layer reextracted with dichloromethane, the organic layers combined, dried over magnesium sulfate, filtered, and the solvent evaporated under reduced pressure. The crude product was purified via silica gel chromatography with ethyl acetate. Fractions containing the product were combined, the solvent evaporated to yield 0.186 g of the desired product.
Workup
- washwas washed with aqueous sodium hydrogencarbonate
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- customthe solvent evaporated under reduced pressure
- customThe crude product was purified via silica gel chromatography with ethyl acetate
- additionFractions containing the product
- customthe solvent evaporated
Sources & evidence
- ORD record
- ord-0249cf4f1e534889a8f4ee958bfa8a2c
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07851463B2
Reaction notes
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