Cesium carbonate → (2R)-1-[4-(4-iodophenoxy)butyl]-2-methylpyrrolidine

HRID 1928654Notes

Reaction equation

HRID 1928654 reaction equation
[CH3:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][NH:3]1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:14][CH2:15][CH2:16][CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([I:25])=[CH:21][CH:20]=1>C(#N)C>[I:25][C:22]1[CH:23]=[CH:24][C:19]([O:18][CH2:17][CH2:16][CH2:15][CH2:14][N:3]2[CH2:4][CH2:5][CH2:6][C@H:2]2[CH3:1])=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 641544(R)-2-MethylpyrrolidineHCID 581868981-(4-Chlorobutoxy)-4-iodobenzene

Product 1

HCID 58186896(2R)-1-[4-(4-iodophenoxy)butyl]-2-methylpyrrolidineYield 89%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of (2R)-2-methylpyrrolidine (0.8 g) and cesium carbonate (1.7 g) in acetonitrile (5 mL), 1-(4-chlorobutoxy)-4-iodobenzene obtained in Example 61-(1) (1.4 g) was added and the mixture was heated to 100° C., at which it was stirred for 9 hours. The reaction mixture was cooled to room temperature and filtered to remove insoluble materials, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by NH-type silica gel column chromatography (eluting solvent: n-hexane:ethyl acetate=9:1 to 1:1) to give the titled compound (1.4 g, 89%) as a colorless oil.

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was cooled to room temperature
  3. filtrationfiltered
  4. customto remove insoluble materials
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe resulting residue was purified by NH-type silica gel column chromatography (eluting solvent: n-hexane:ethyl acetate=9:1 to 1:1)

Sources & evidence

ORD record
ord-7d1eb45a9300477ab8f4bb8eb8f4c8e9
Source dataset
uspto-grants-2012_05
Patent number
US08183387B2

Reaction notes

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