Piperidine → (5S)-5-(piperidin-1-ylmethyl)pyrrolidin-2-one

HRID 548625Notes

Reaction equation

HRID 548625 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CC1C=CC(S(O[CH2:18][C@@H:19]2[CH2:23][CH2:22][C:21](=[O:24])[NH:20]2)(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[N:1]1([CH2:18][C@H:19]2[NH:20][C:21](=[O:24])[CH2:22][CH2:23]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 11430Potassium CarbonateHCID 2734055[(2S)-5-oxopyrrolidin-2-yl]methyl 4-methylbenzene-1-sulfonate

Product 1

HCID 57550249(5S)-5-(piperidin-1-ylmethyl)pyrrolidin-2-oneYield 100%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Piperidine a14 (0.7 g, 8.3 mmol, 1.5 eq) is added to a suspension of [(2S)-5-oxopyrrolidin-2-yl]methyl 4-methylbenzenesulfonate a13 (1.5 g, 5.56 mmol, 1 eq) and potassium carbonate (1.5 g, 11.1 mmol, 2 eq) in acetonitrile (50 ml), and the mixture is stirred at reflux overnight. Potassium carbonate is filtered and the solvent is removed in vacuo. The residue is dissolved in a minimum of dichloromethane, then the organic layer is sonicated and heated to precipitate a white solid which is filtered. The liquid phase is concentrated in vacuo to give 1 g of (5S)-5-(piperidin-1-ylmethyl)pyrrolidin-2-one a15 as a yellow oil.

Workup

  1. temperatureat reflux overnight
  2. filtrationPotassium carbonate is filtered
  3. customthe solvent is removed in vacuo
  4. dissolutionThe residue is dissolved in a minimum of dichloromethane
  5. customthe organic layer is sonicated
  6. temperatureheated
  7. customto precipitate a white solid which
  8. filtrationis filtered
  9. concentrationThe liquid phase is concentrated in vacuo

Sources & evidence

ORD record
ord-274543a02ff94f01b9eb850d1114ab7f
Source dataset
uspto-grants-2011_05
Patent number
US07943605B2

Reaction notes

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