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

HRID 1260264노트

반응식

HRID 1260264 반응식
[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

참가 물질

6

반응물 3

HCID 6422Trifluoroacetic acidHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amine2회HCID 536287222-Methoxy-1-nitro-4-vinylbenzene

생성물 1

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

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-00683ec09d01409599350930976ace5a
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08470810B2

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