2,6-Lutidine → Ethyl 4-[2-(pyrrolidin-1-yl)ethyl]-1H-pyrrole-2-carboxylate

HRID 241717노트

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HRID 241717 반응식
[NH2:1][CH2:2][CH2:3][C:4]1[CH:5]=[C:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[NH:7][CH:8]=1.N1C(C)=C[CH:17]=[CH:16][C:15]=1[CH3:21].BrCCCCBr>CN(C=O)C.C(OCC)(=O)C>[N:1]1([CH2:2][CH2:3][C:4]2[CH:5]=[C:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[NH:7][CH:8]=2)[CH2:17][CH2:16][CH2:15][CH2:21]1

참가 물질

6

반응물 3

HCID 79372,6-LutidineHCID 80561,4-DibromobutaneHCID 66636613ethyl 4-(2-aminoethyl)-1H-pyrrole-2-carboxylate

생성물 1

HCID 66636407Ethyl 4-[2-(pyrrolidin-1-yl)ethyl]-1H-pyrrole-2-carboxylate

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

To a solution of the product obtained in Step G (1.3 g) in DMF (134 ml) there are added 2,6-lutidine (4.15 ml) and 1,4-dibromo-butane (4.68 ml). The reaction mixture is stirred at 80° C. for 12 hours and at ambient temperature overnight. The reaction mixture is diluted with 600 ml of ethyl acetate. The organic phase is washed with saturated aqueous NaHCO3 solution, with water and with saturated aqueous NaCl solution, dried over magnesium sulphate, filtered and evaporated to dryness. The residue obtained is purified on silica gel (SiO2: gradient CH2Cl2/MeOH with the addition of 1.4N NH3 in the MeOH) to yield the title product, which is used directly in the next Step.

후처리

  1. washThe organic phase is washed with saturated aqueous NaHCO3 solution, with water and with saturated aqueous NaCl solution
  2. dry with materialdried over magnesium sulphate
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe residue obtained
  6. customis purified on silica gel (SiO2
  7. additiongradient CH2Cl2/MeOH with the addition of 1.4N NH3 in the MeOH)

출처 및 근거

ORD 기록
ord-ceb3264e88064f709bc5b69839cefb30
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08653073B2

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