Triethylamine → HCID 54075416, compound

HRID 397609Notes

Reaction equation

HRID 397609 reaction equation
C(N(CC)CC)C.[C:8]([O:12][C:13]([N:15]1[CH2:20][CH2:19][C:18](=[O:21])[CH:17]([CH:22](O)[CH3:23])[CH2:16]1)=[O:14])([CH3:11])([CH3:10])[CH3:9].CS(Cl)(=O)=O>C(Cl)Cl>[C:8]([O:12][C:13]([N:15]1[CH2:20][CH2:19][C:18](=[O:21])[C:17](=[CH:22][CH3:23])[CH2:16]1)=[O:14])([CH3:11])([CH3:10])[CH3:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 23000869HCID 23000869, compound

Product 1

HCID 54075416HCID 54075416, compoundYield 77.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.77 g (7.6 mmol) of triethylamine were added to a 20 ml methylene chloride solution of 1.86 g (7.6 mmol) of the 1-(t-butoxycarbonyl)-3-(1-hydroxyethyl)-4-piperidone obtained above. Under ice cooling, 0.88 g (7.6 mmol) of methanesulfonyl chloride were added and the resulting mxiture was stirred at room temperature for 1 hour. The solvent was distilled off under reduced pressure. Ethyl acetate was added to the residue. The solid thus precipitated was filled out, followed by concentration under reduced pressure again. The concentrate was then dissolved in 20 ml of chloroform, followed by the addition of 1.16 g (7.6 mmol) of 1,8-diazabicyclo[5.4.0]under-7-ene (DBU) at room temperature. The mixture was stirred for 2 hours at the same temperature. After completion of the reaction, the reaction mixture was concentrated under reduced pressure. The residue was subjected to chromatography on a silica gel column (eluting solvent: toluene/ethyl acetate=19/1), whereby 1.32 g (yield: 77.2%) of the title compound were obtained as a colorless oil.

Workup

  1. customobtained above
  2. distillationThe solvent was distilled off under reduced pressure
  3. additionEthyl acetate was added to the residue
  4. customThe solid thus precipitated
  5. additionwas filled out
  6. concentrationfollowed by concentration under reduced pressure again
  7. dissolutionThe concentrate was then dissolved in 20 ml of chloroform
  8. stirringThe mixture was stirred for 2 hours at the same temperature
  9. customAfter completion of the reaction
  10. concentrationthe reaction mixture was concentrated under reduced pressure
  11. washThe residue was subjected to chromatography on a silica gel column (eluting solvent: toluene/ethyl acetate=19/1)

Sources & evidence

ORD record
ord-675c486cee6a4c54bcaf36b66032c479
Source dataset
uspto-grants-2003_08
Patent number
US06610708B1

Reaction notes

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