Trifluoroacetic acid → 1-Benzyl-3-(3-methoxy-4-nitro-phenyl)-pyrrolidine

HRID 1260264Notes

Reaction equation

HRID 1260264 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH:9]=[CH2:10])[CH:6]=[CH:5][C:4]=1[N+:11]([O-:13])=[O:12].FC(F)(F)C(O)=O.[CH2:21]([N:28]([CH2:34]OC)[CH2:29][Si](C)(C)C)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>ClCCl.C(OC(=O)C)C>[CH2:21]([N:28]1[CH2:29][CH2:10][CH:9]([C:7]2[CH:6]=[CH:5][C:4]([N+:11]([O-:13])=[O:12])=[C:3]([O:2][CH3:1])[CH:8]=2)[CH2:34]1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amine2×HCID 536287222-Methoxy-1-nitro-4-vinylbenzene

Product 1

HCID 574700891-Benzyl-3-(3-methoxy-4-nitro-phenyl)-pyrrolidineYield 127.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Methoxy-1-nitro-4-vinyl-benzene (435 mg, 2.43 mmol) was dissolved in dichloromethane (2 ml), trifluoro acetic acid (80 μl, 1.0 mmol) was added, followed by slow addition of N-benzyl-N-(methoxymethyl)-N-trimethylsilylmethylamine (715 mg, 3.01 mmol). Stirring was continued for 2 h at room temperature. Another portion of N-benzyl-N-(methoxymethyl)-N-trimethylsilylmethylamine (300 mg, 1.26 mmol) was added and stirring continued for another 30 minutes. The reaction mixture was diluted with ethylacetate (25 ml), washed with aqueous NaHCO3 (15 ml). The organic layer was dried over magnesium sulfate, filtered, and the solvent evaporated under reduced pressure to yield an oil (970 mg). The crude product was purified via silica gel chromatography with cyclohexane/ethyl acetate (gradient 0-50%). Fractions containing the product were combined, the solvent evaporated to yield an oil (320 mg, 46%).

Workup

  1. stirringstirring
  2. waitcontinued for another 30 minutes
  3. washwashed with aqueous NaHCO3 (15 ml)
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-00683ec09d01409599350930976ace5a
Source dataset
uspto-grants-2013_06
Patent number
US08470810B2

Reaction notes

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