Pyrrolidine → 3-Bromo-5-(pyrrolidin-1-ylmethyl)pyridine

HRID 546643Notes

Reaction equation

HRID 546643 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=O)[CH:5]=[N:6][CH:7]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[NH:24]1[CH2:28][CH2:27][CH2:26][CH2:25]1>ClCCCl>[Br:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]([CH2:8][N:24]2[CH2:28][CH2:27][CH2:26][CH2:25]2)[CH:3]=1

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 27847345-Bromo-3-pyridinecarboxaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 212559453-Bromo-5-(pyrrolidin-1-ylmethyl)pyridine

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 5-bromo-3-pyridinecarboxaldehyde in 20 mL of 1,2-dichloroethane are successively added, under argon, 4.55 g of sodium triacetoxyborohydride and 0.94 mL of pyrrolidine. The reaction mixture is stirred at room temperature for 3 hours and then washed with saturated sodium hydrogen carbonate solution, with water and with saturated sodium chloride solution, dried over magnesium sulphate, filtered and concentrated under reduced pressure. The residue is purified by chromatography on a column of silica, eluting with a mixture of ethyl acetate and cyclohexane (80/20 by volume) to give 1.4 g of 3-Bromo-5-pyrrolidin-1-ylmethylpyridine in the form of a pale yellow oil.

Workup

  1. washwashed with saturated sodium hydrogen carbonate solution, with water and with saturated sodium chloride solution
  2. dry with materialdried over magnesium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by chromatography on a column of silica
  6. washeluting with a mixture of ethyl acetate and cyclohexane (80/20 by volume)

Sources & evidence

ORD record
ord-57125a8d6a064790a21575419153c8d7
Source dataset
uspto-grants-2011_05
Patent number
US07935819B2

Reaction notes

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