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

HRID 2216368Notes

Reaction equation

HRID 2216368 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.C1CCN2C(=NCCC2)CC1>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 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 982104-Hydroxypyrrolidine

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

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

Workup

  1. temperaturewas heated
  2. customThe reaction mixture was separated with ethyl acetate-water
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5972ed998fd5418cb95cef454b659941
Source dataset
uspto-grants-2006_09
Patent number
US07112593B2

Reaction notes

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