2,6-Dibromopyridine → 1-(6-Bromopyridin-2-yl)pyrrolidin-3-ol

HRID 1359336Notes

Reaction equation

HRID 1359336 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1.[OH:9][CH:10]1[CH2:14][CH2:13][NH:12][CH2:11]1.CCCCCCC=CCCC>O1CCCC1>[Br:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([N:12]2[CH2:13][CH2:14][CH:10]([OH:9])[CH2:11]2)[N:3]=1

Participants

5

Reactant 3

HCID 122742,6-DibromopyridineHCID 982104-HydroxypyrrolidineHCID 136496Undec-4-ene

Product 1

HCID 219422981-(6-Bromopyridin-2-yl)pyrrolidin-3-olYield 100.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5.7 g of 2,6-dibromopyridine, 2.5 g of 3-hydroxypyrrolidine, 3.6 ml of 1,8-diazbicyclo[5.4.0]-7-undecene (DBU) and 20 ml of tetrahydrofuran was heated under stirring for 11 hours in an oil bath kept at 70° C. The mixture was partitioned between ethyl acetate-water, and the organic layer was washed with water and brine, dried over anhydrous magnesium sulfate and then concentrated. The residue was subjected to silica gel column chromatography using 10-30% ethyl acetate/hexane, to give 5.9 g of 2-bromo-6-(3-hydroxypyrrolidine-1-yl)pyridine.

Workup

  1. temperaturewas heated
  2. customkept at 70° C
  3. customThe mixture was partitioned between ethyl acetate-water
  4. washthe organic layer was washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7d75fa03e0904cdf9695802a44bc7e88
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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