Potassium Carbonate → 4-(Pyrrolidin-1-ylmethyl)-1,3-oxazolidin-2-one

HRID 548632Notes

Reaction equation

HRID 548632 reaction equation
C(=O)([O-])[O-].[K+].[K+].[NH:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1.CC1C=CC(S(O[CH2:23][CH:24]2[CH2:28][O:27][C:26](=[O:29])[NH:25]2)(=O)=O)=CC=1>C(#N)C>[N:7]1([CH2:23][CH:24]2[CH2:28][O:27][C:26](=[O:29])[NH:25]2)[CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 14456891(2-Oxo-1,3-oxazolidin-4-yl)methyl 4-methylbenzene-1-sulfonate

Product 1

HCID 575502564-(Pyrrolidin-1-ylmethyl)-1,3-oxazolidin-2-oneYield 92%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Potassium carbonate (0.62 g, 4.5 mmol, 2 eq) and pyrrolidine (0.28 ml, 3.37 mmol, 1.5 eq) are added to a solution of (2-oxo-1,3-oxazolidin-4-yl)methyl 4-methylbenzenesulfonate a91 (0.62 g, 2.25 mmol, 1 eq) in acetonitrile (22 ml). The mixture is heated at reflux overnight. After cooling, the mixture is filtered and the solid is washed with acetonitrile. The acetonitrile phases are concentrated in vacuo. The residue is taken up in dichloromethane, heated, filtered and washed with dichloromethane. The dichloromethane phases are concentrated in vacuo to give 0.35 g of 4-(pyrrolidin-1-ylmethyl)-1,3-oxazolidin-2-one a92 as a yellow oil.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux overnight
  3. temperatureAfter cooling
  4. filtrationthe mixture is filtered
  5. washthe solid is washed with acetonitrile
  6. concentrationThe acetonitrile phases are concentrated in vacuo
  7. temperatureheated
  8. filtrationfiltered
  9. washwashed with dichloromethane
  10. concentrationThe dichloromethane phases are concentrated in vacuo

Sources & evidence

ORD record
ord-863f414d56864102ba5e8c423b01b6ad
Source dataset
uspto-grants-2011_05
Patent number
US07943605B2

Reaction notes

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