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

HRID 1093981Notes

Reaction equation

HRID 1093981 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-7f2272440eb442bb912a9b9628640ba4
Source dataset
uspto-grants-2012_03
Patent number
US08133889B2

Reaction notes

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