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

HRID 1093982ノート

反応式

HRID 1093982 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-da24164dbbd54fe99c430ee106dcde96
出典データセット
uspto-grants-2012_03
特許番号
US08133889B2

反応ノート

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