Methyl iodide → (S)-2-{2-[2-(3-Methoxyphenyl)ethyl]phenoxymethyl}-1-methylpyrrolidine

HRID 743283Notes

Reaction equation

HRID 743283 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH2:15][CH2:16][C:17]2[CH:29]=[CH:28][CH:27]=[CH:26][C:18]=2[O:19][CH2:20][C@@H:21]2[CH2:25][CH2:24][CH2:23][NH:22]2)[CH:12]=[CH:13][CH:14]=1.CI>CC(N(C)C)=O.C(OCC)(=O)C>[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH2:15][CH2:16][C:17]2[CH:29]=[CH:28][CH:27]=[CH:26][C:18]=2[O:19][CH2:20][C@@H:21]2[CH2:25][CH2:24][CH2:23][N:22]2[CH3:1])[CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 53750852(S)-2-{2-[2-(3-Methoxyphenyl)ethyl]phenoxymethyl}pyrrolidine

Product 1

HCID 10498838(S)-2-{2-[2-(3-Methoxyphenyl)ethyl]phenoxymethyl}-1-methylpyrrolidineYield 104.5%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

130 mg of potassium carbonate were added to a solution of 500 mg of (S)-2-{2-[2-(3-methoxyphenyl)ethyl]phenoxymethyl}pyrrolidine [prepared as described in Example 57(b)] in 5 ml of dimethylacetamide, and the resulting mixture was stirred at room temperature for 5 minutes, after which 288 mg of methyl iodide were added. The reaction mixture was then stirred at room temperature for 5 minutes, after which it was diluted with ethyl acetate. The diluted solution was then washed with water and with a saturated aqueous solution of sodium chloride, in that order, and dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through silica gel, using a 20:1 by volume mixture of methylene chloride and methanol as the eluent, to give 320 mg (yield 61%) of the title compound as a colorless oil.

Workup

  1. stirringThe reaction mixture was then stirred at room temperature for 5 minutes
  2. washThe diluted solution was then washed with water and with a saturated aqueous solution of sodium chloride, in that order
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was then removed by distillation under reduced pressure
  5. customthe resulting residue was purified by column chromatography through silica gel
  6. additionby volume mixture of methylene chloride and methanol as the eluent

Sources & evidence

ORD record
ord-32357095520545ca9af602d68b436015
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

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