2,5-Dibromopyridine → (3R)-1-(5-Bromopyridin-2-yl)pyrrolidin-3-ol

HRID 2428194Notes

Reaction equation

HRID 2428194 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[CH2:9]1[C@@H:13]([OH:14])[CH2:12][NH:11][CH2:10]1>C1(C)C=CC=CC=1>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([N:11]2[CH2:10][CH2:9][C@@H:13]([OH:14])[CH2:12]2)=[N:3][CH:4]=1

Participants

4

Reactant 2

HCID 693532,5-DibromopyridineHCID 2759337(R)-3-Pyrrolidinol

Product 1

HCID 57365913(3R)-1-(5-Bromopyridin-2-yl)pyrrolidin-3-olYield 84.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2,5-dibromopyridine (10.0 g, 42.2 mmol) and (R)-hydroxypyrrolidine (11.0 g, 126 mmol) in toluene (50 mL) was heated to reflux overnight. The mixture was allowed to cool to rt, and the solvents were removed under reduced pressure. The residue was dissolved with EtOAc (150 mL), and the mixture was washed with aq. 10% K2CO3. The org. layer was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (heptane→heptane/EtOAc 1:2) yielded the title compound (8.63 g, 84%). LC-MS: tR=0.48 min; ES+: 243.15.

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. customthe solvents were removed under reduced pressure
  4. dissolutionThe residue was dissolved with EtOAc (150 mL)
  5. washthe mixture was washed with aq. 10% K2CO3
  6. dry with materiallayer was dried over MgSO4
  7. filtrationfiltered
  8. customthe solvents were removed under reduced pressure
  9. customPurification of the residue by FC (heptane→heptane/EtOAc 1:2)

Sources & evidence

ORD record
ord-08237e985b2e4885afd1e89167922b6a
Source dataset
uspto-grants-2011_06
Patent number
US07968720B2

Reaction notes

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