1,1,3,3-Tetramethylguanidine → 1,1-Dimethylethyl 4-[(2,4-dioxo-1,3-oxazolidin-3-yl)methyl]piperidine-1-carboxylate

HRID 505868Notes

Reaction equation

HRID 505868 reaction equation
CS(O[CH2:6][CH:7]1[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]1)(=O)=O.[O:20]1[CH2:24][C:23](=[O:25])[NH:22][C:21]1=[O:26].CN(C)C(N(C)C)=N>O1CCCC1.CN(C)C=O>[O:26]=[C:21]1[N:22]([CH2:6][CH:7]2[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]2)[C:23](=[O:25])[CH2:24][O:20]1

Participants

6

Reactant 3

HCID 664601,1,3,3-TetramethylguanidineHCID 973892,4-OxazolidinedioneHCID 2765838Tert-butyl 4-(methylsulfonyloxymethyl)piperidine-1-carboxylate

Product 1

HCID 684647311,1-Dimethylethyl 4-[(2,4-dioxo-1,3-oxazolidin-3-yl)methyl]piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 13.60 g (46.36 mmol) of 1,1-dimethylethyl 4-{[(methylsulphonyl)oxy]methyl}piperidine-1-carboxylate, prepared in step 2.1., 9.37 g (92.72 mmol) of 1,3-oxazolidine-2,4-dione and 16.02 g (139.08 mmol) of 1,1,3,3-tetramethylguanidine in a mixture of 180 ml of tetrahydrofuran and 30 ml of dimethylformamide is heated at reflux for 24 hours. It is allowed to return to ambient temperature and is concentrated under reduced pressure. The residue is taken up in dichloromethane and water and the aqueous phase is separated off and extracted twice with dichloromethane. The combined organic phases are washed with saturated aqueous sodium chloride solution and dried over sodium sulphate. Following evaporation of the solvent, the residue obtained is purified by chromatography on silica gel, eluting with a 98/2 then 95/5 mixture of dichloromethane and methanol.

Workup

  1. customprepared in step 2.1
  2. temperatureis heated
  3. temperatureat reflux for 24 hours
  4. customto return to ambient temperature
  5. concentrationis concentrated under reduced pressure
  6. customwater and the aqueous phase is separated off
  7. extractionextracted twice with dichloromethane
  8. washThe combined organic phases are washed with saturated aqueous sodium chloride solution
  9. dry with materialdried over sodium sulphate
  10. customevaporation of the solvent
  11. customthe residue obtained
  12. customis purified by chromatography on silica gel
  13. washeluting with a 98/2
  14. addition95/5 mixture of dichloromethane and methanol

Sources & evidence

ORD record
ord-b326d9d21c374e249ba9cb52712bdf58
Source dataset
uspto-grants-2010_08
Patent number
US07781590B2

Reaction notes

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