Methyl iodide → (2S, 4S)-4-(4-methoxybenzylthio)-2-methoxycarbonyl-1-methylpyrrolidine

HRID 5084Notes

Reaction equation

HRID 5084 reaction equation
[C:1](=O)(O)[O-].[Na+].CI.[CH3:8][O:9][C:10]1[CH:26]=[CH:25][C:13]([CH2:14][S:15][C@@H:16]2[CH2:20][NH:19][C@H:18]([C:21]([O:23][CH3:24])=[O:22])[CH2:17]2)=[CH:12][CH:11]=1>CN(C)C=O>[CH3:8][O:9][C:10]1[CH:11]=[CH:12][C:13]([CH2:14][S:15][C@@H:16]2[CH2:20][N:19]([CH3:1])[C@H:18]([C:21]([O:23][CH3:24])=[O:22])[CH2:17]2)=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 516892Sodium Bicarbonate2×HCID 15200411(2S, 4S)-4-(4-Methoxybenzylthio)-2-methoxycarbonylpyrrolidine

Product 1

HCID 57321322(2S, 4S)-4-(4-methoxybenzylthio)-2-methoxycarbonyl-1-methylpyrrolidineYield 27.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.18 g of sodium bicarbonate and 0.876 ml of methyl iodide were added, whilst ice-cooling, to a solution of 3.3 g of (2S, 4S)-4-(4-methoxybenzylthio)-2-methoxycarbonylpyrrolidine [prepared as described in step (9) above] dissolved in 30 ml of dry dimethylformamide, and the mixture was stirred at room temperature for 5 hours. At the end of this time, the reaction mixture was poured into a saturated aqueous solution of sodium bicarbonate and extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography over silica gel (eluted with a 1:2 by volume mixture of ethyl acetate and benzene), to afford 968 mg of the title compound as an oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with an aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed by distillation under reduced pressure
  5. customThe residue was purified by column chromatography over silica gel (
  6. washeluted with a 1:2 by volume mixture of ethyl acetate and benzene),

Sources & evidence

ORD record
ord-2d65ae8fa14242fd82d46e52981a6b6d
Source dataset
uspto-grants-1993_09
Patent number
US05242914

Reaction notes

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