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

HRID 385923

Reaction equation

HRID 385923 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1.[NH:9]1[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10]1.CCCCCCC=CCCC>C1COCC1.C(OCC)(=O)C>[Br:8][C:4]1[N:3]=[C:2]([N:9]2[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10]2)[CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 3

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

Product 1

HCID 219422981-(6-Bromopyridin-2-yl)pyrrolidin-3-ol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2,6-dibromopyridine (2.37 g, 0.01 mol), pyrrolidin-3-ol (1.0 g, 0.01 mol), 1,8-diazabicclo[5.4.0)-7-undecene (1.5 mL) in 10 mL of THF was heated at 70° C. under a nitrogen atmosphere for 11 hours. The reaction mixture was then cooled to room temperature, diluted with ethyl acetate (30 mL). The resulting solution was washed with water and brine, dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography (10-30% ethyl acetate/hexane) to give the title compound.

Workup

  1. washThe resulting solution was washed with water and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography (10-30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-23d8af70e5b34017a33c984f345e567d
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Linked notes

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