Pyrrolidine → 5-Bromo-2-(pyrrolidin-1-ylmethyl)pyridine

HRID 546641Notes

Reaction equation

HRID 546641 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]=O)=[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.ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][N:24]2[CH2:28][CH2:27][CH2:26][CH2:25]2)=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 31268PyrrolidineHCID 5049666Sodium triacetoxyborohydrideHCID 98775625-Bromopyridine-2-carbaldehyde

Product 1

HCID 230909345-Bromo-2-(pyrrolidin-1-ylmethyl)pyridine

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2 g of 5-bromo-2-formylpyridine 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 1 hour and then diluted with dichloromethane and the organic phase is 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 dichloromethane and methanol (98/2 by volume) to give 0.93 g of 5-bromo-2-pyrrolidin-1-ylmethylpyridine, the characteristics of which are as follows:

Workup

  1. washthe organic phase is washed 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 dichloromethane and methanol (98/2 by volume)

Sources & evidence

ORD record
ord-da6421b55cb141f39411849a8c3fb49a
Source dataset
uspto-grants-2011_05
Patent number
US07935819B2

Reaction notes

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