Hydrochloric Acid → (R)-5-(Pyrrolidin-3-yl)-2H-tetrazole

HRID 1040420Notes

Reaction equation

HRID 1040420 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][C@@H:10]([C:13]2[N:14]=[N:15][NH:16][N:17]=2)[CH2:9]1)=O)(C)(C)C.Cl.O1CCOCC1>CO>[NH:8]1[CH2:12][CH2:11][C@@H:10]([C:13]2[N:14]=[N:15][NH:16][N:17]=2)[CH2:9]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 58430906tert-Butyl (R)-3-(2H-tetrazol-5-yl)pyrrolidine-1-carboxylate

Product 1

HCID 21025944(R)-5-(Pyrrolidin-3-yl)-2H-tetrazoleYield 63%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(R)-3-(2H-Tetrazol-5-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester (600 mg, 2.51 mmol) was dissolved in methanol (20 mL), 4M HCl in dioxane (1.13 ml, 4.52 mmol) was then added dropwise. The solution was stirred overnight. The reaction was concentrated in vacuo. The residue was purified by reverse phase HPLC to afford (R)-5-pyrrolidin-3-yl-2H-tetrazole (220 mg, 1.58 mmol, 63%) as a white solid.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customThe residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-69d661ae2896405fbf64328ef0f9f503
Source dataset
uspto-grants-2013_10
Patent number
US08552205B2

Reaction notes

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