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

HRID 1260264ノート

反応式

HRID 1260264 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-00683ec09d01409599350930976ace5a
出典データセット
uspto-grants-2013_06
特許番号
US08470810B2

反応ノート

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