Hydrochloric Acid → 1-(pyrrolidin-3-yl)-1H-1,2,3-triazole-4-carboxylic acid hydrochloride

HRID 1743001Notes

Reaction equation

HRID 1743001 reaction equation
[ClH:1].C([N:9]1[CH2:13][CH2:12][CH:11]([N:14]2[CH:18]=[C:17]([C:19]([OH:21])=[O:20])[N:16]=[N:15]2)[CH2:10]1)C1C=CC=CC=1.Cl>CO.[Pd]>[ClH:1].[C:19]([C:17]1[N:16]=[N:15][N:14]([CH:11]2[CH2:12][CH2:13][NH:9][CH2:10]2)[CH:18]=1)([OH:21])=[O:20]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 19006014N-benzyl-3-(4-carboxy-1,2,3-triazol-1-yl)pyrrolidine hydrochloride

Product 1

HCID 190059671-(pyrrolidin-3-yl)-1H-1,2,3-triazole-4-carboxylic acid hydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of N-benzyl-3-(4-carboxy-1,2,3-triazol-1-yl)pyrrolidine hydrochloride (1 g, 0.0033 mol) in methanol (50 ml) was added 10% Pd/C (100 mg) and conc. HCl (0.5 ml). The suspension was hydrogenated at r.t. and 50 psi pressure for 20 hrs. The Pd/C was removed by filtration and the solution was concentrated. The residue was recrystallized from methanol/ether to obtain white crystalline title compound. Yield: 650 mg (93.25%). 1H NMR (D2O) δ: 2.51-3.56 (m, 2H), 3.62-3.75 (m, 2H), 3.92-4.00 (m, 2H), 5.52-5.67 (m, 1H), 8.67 (s, 1H).

Workup

  1. customwas hydrogenated at r.t.
  2. customThe Pd/C was removed by filtration
  3. concentrationthe solution was concentrated
  4. customThe residue was recrystallized from methanol/ether

Sources & evidence

ORD record
ord-5222646fcecf469987b93e251d85dda3
Source dataset
uspto-grants-1994_08
Patent number
US05342846

Reaction notes

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