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

HRID 44262Notes

Reaction equation

HRID 44262 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-2905611c12ee4473bc844e963fa5fea6
Source dataset
uspto-grants-2013_09
Patent number
US08541412B2

Reaction notes

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