Triethylamine → HCID 21963748, compound

HRID 2212081Notes

Reaction equation

HRID 2212081 reaction equation
[C:1]1([S:7]([C:10]2([CH2:15][CH2:16][CH2:17]O)[CH2:14][CH:13]=[CH:12][CH2:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.CS(Cl)(=O)=O.[CH3:31][C:32]1[CH2:33][NH:34][CH2:35][CH2:36][C:37]=1[CH3:38].C(=O)([O-])[O-].[K+].[K+]>ClCCl.O>[C:1]1([S:7]([C:10]2([CH2:15][CH2:16][CH2:17][N:34]3[CH2:33][C:32]([CH3:31])=[C:37]([CH3:38])[CH2:36][CH2:35]3)[CH2:14][CH:13]=[CH:12][CH2:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 10997188HCID 10997188, compoundHCID 21963772HCID 21963772, compound

Product 1

HCID 21963748HCID 21963748, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-(1-benzenesulphonylcyclopent-3-enyl)propan-1-ol (56 mg, 0.21 mmol) and triethylamine (41 μL, 0.29 mmol) in dichloromethane (5 ml) was cooled to 0° C. and treated with methanesulphonyl chloride (21 μL, 0.27 mmol). The mixture was allowed to warm to room temperature and stirred for 30 minutes, then diluted with water and extracted with ethyl acetate. The combined organic layers were dried (MgSO4) and concentrated in vacuo. The residue was dissolved in acetonitrile (5 ml), treated with 3,4-dimethyl-1,2,5,6-tetrahydropyridine (397 mg, 0.32 mmol) and potassium carbonate (58 mg, 0.42 mmol) and heated at 60° C. for 3 hours. The mixture was diluted with water and extracted with ethyl acetate. The combined organic layers were dried (MgSO4) and concentrated in vacuo. The residue was purified by preparative thin layer chromatography, eluting with 5% methanol/dichloromethane, to give the title compound.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in acetonitrile (5 ml)
  5. temperatureheated at 60° C. for 3 hours
  6. extractionextracted with ethyl acetate
  7. dry with materialThe combined organic layers were dried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by preparative thin layer chromatography
  10. washeluting with 5% methanol/dichloromethane

Sources & evidence

ORD record
ord-0e6f2490dd494bd3b9b642b075fe5097
Source dataset
uspto-grants-2006_09
Patent number
US07101892B2

Reaction notes

Loading…