4-Bromoaniline → 1-(4-Bromophenyl)-2,5-bis(4-nitrophenyl)pyrrolidine

HRID 2364823

반응식

HRID 2364823 반응식
CS(O[CH:6]([C:24]1[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=1)[CH2:7][CH2:8][CH:9](OS(C)(=O)=O)[C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=1)(=O)=O.[Br:33][C:34]1[CH:40]=[CH:39][C:37]([NH2:38])=[CH:36][CH:35]=1>CN(C=O)C>[Br:33][C:34]1[CH:40]=[CH:39][C:37]([N:38]2[CH:9]([C:10]3[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=3)[CH2:8][CH2:7][CH:6]2[C:24]2[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=2)=[CH:36][CH:35]=1

참가 물질

4

반응물 2

HCID 78074-BromoanilineHCID 596171791,4-Bis(4-nitrophenyl)butane-1,4-diyl dimethanesulfonate

생성물 1

HCID 866491071-(4-Bromophenyl)-2,5-bis(4-nitrophenyl)pyrrolidine수율 11%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
50 °C

실험 절차

The product from Example 1C (0.7 g, 1.433 mmol) and 4-bromoaniline (2.54 g, 14.33 mmol) were suspended in DMF (6 mL) and stirred at 50° C. overnight. The resulting mixture was partitioned between ethyl acetate (100 mL) and water (50 mL). The organic phase was washed with 1N HCl (2×50 mL) followed by a brine wash then dried over MgSO4 filtered and concentrated. The crude product was purified by chromatography on silica gel using a solvent gradient of 2-50% ethyl acetate in hexane to give the title compound as a mixture of stereoisomers (74.4 mg, 11% yield).

후처리

  1. customThe resulting mixture was partitioned between ethyl acetate (100 mL) and water (50 mL)
  2. washThe organic phase was washed with 1N HCl (2×50 mL)
  3. washwash
  4. dry with materialthen dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by chromatography on silica gel using a solvent gradient of 2-50% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-36f38618314947bdb466d6be96373f54
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08691938B2

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