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

HRID 215776Notes

Reaction equation

HRID 215776 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-2a14b215c4e9446ea8584fe8207de3a1
Source dataset
uspto-grants-2012_06
Patent number
US08193176B2

Reaction notes

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