Ammonia → ethyl 4-(2-aminoethyl)-1H-pyrrole-2-carboxylate

HRID 44261Notes

Reaction equation

HRID 44261 reaction equation
[C:1]([CH2:3][C:4]1[CH:5]=[C:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[NH:7][CH:8]=1)#[N:2].N>CO.O=[Pt]=O>[NH2:2][CH2:1][CH2:3][C:4]1[CH:5]=[C:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[NH:7][CH:8]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 66636709Ethyl 4-(cyanomethyl)-1H-pyrrole-2-carboxylate

Product 1

HCID 66636613ethyl 4-(2-aminoethyl)-1H-pyrrole-2-carboxylate

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 345198Adams' catalystSolvent

Procedure

To a solution of the product obtained in Step F (7.45 g) in MeOH (1.5 L) there are added 223 ml of a 1.4N solution of NH3 in MeOH and PtO2 (5.2 g). The reaction mixture is placed under an atmosphere of hydrogen and is then stirred for 20 hours at ambient temperature. After filtration and evaporation 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. filtrationAfter filtration and evaporation to dryness
  2. customthe residue obtained
  3. customis purified on silica gel (SiO2
  4. additiongradient CH2Cl2/MeOH with the addition of 1.4N NH3 in the MeOH)

Sources & evidence

ORD record
ord-b0ea47992e4c4bc1bb3aaa1d2ed9c8b1
Source dataset
uspto-grants-2013_09
Patent number
US08541412B2

Reaction notes

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