Dimethyl Sulfoxide → HCID 22884890, compound

HRID 1599375Notes

Reaction equation

HRID 1599375 reaction equation
[CH2:1]=[CH:2][CH:3]1[CH:8]2[CH2:9][CH:10]([C@H:11]([OH:23])[C:12]3[CH:21]=[CH:20][N:19]=[C:18]4[C:13]=3[CH:14]=[C:15]([OH:22])[CH:16]=[CH:17]4)[N:5]([CH2:6][CH2:7]2)[CH2:4]1.CS(C)=O.C([Li])C[CH2:30][CH3:31].[I:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36]>ClCCl.C(OCC)(=O)C.O>[I-:33].[CH:2]([CH:3]1[CH:8]2[CH2:7][CH2:6][N@+:5]([CH2:34][C:35]([O:37][CH2:30][CH3:31])=[O:36])([CH:10]([CH:11]([OH:23])[C:12]3[C:13]4[C:18](=[CH:17][CH:16]=[C:15]([O:22][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH:14]=4)[N:19]=[CH:20][CH:21]=3)[CH2:9]2)[CH2:4]1)=[CH2:1]

Participants

8

Reactant 4

HCID 679Dimethyl SulfoxideHCID 12183Ethyl iodoacetateHCID 51196O-DesmethylquinidineHCID 178418339Butyllithium

Product 1

HCID 22884890HCID 22884890, compoundYield 41%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 1-l 3-necked, round-bottomed flask equipped with a magnetic stirrer was charged with 2.0 g (6.44 mol) of 6-hydroxycinchonine (1) and 10 ml of DMSO which had been dried over molecular sieves. To the stirred solution was added very slowly over a period of 0.5 h 2.8 ml (7.0 mmol) of n-butyl lithium (2.5M/hexane, Aldrich). The reaction flask was cooled with an ice-water bath and then treated with 1.6 ml (13.57 mmol) of ethyl iodoacetate. The temperature was allowed to rise to room temperature over a period of 2 h and the mixture was stirred at room temperature for 1 h. The reaction mixture was poured into 65 ml of deionized water and 15 ml of ethyl acetate during which some of the product oiled out. 100 ml of dichloromethane was added to dissolve the oily product and produce two layers. The heterogeneous brown mixture was concentrated under reduced pressure to remove the organic solvents during which the product precipitated. The mixture was left to stand overnight in the refrigerator. The precipitate was collected and washed with ETOAc and yielded 1.6 g (41%) of (S)-8-ethenyl-2-[hydroxy-6-(2-ethoxy-2-oxoethoxy)-4-quinolinylmethyl]-1-(2-ethoxy-2-oxoethyl)azoniabicyclo[2.2.2]octane iodide as an off-white solid. NMR, IR and MS data confirmed compound identity.

Workup

  1. customA 1-l 3-necked, round-bottomed flask equipped with a magnetic stirrer
  2. customhad been dried over molecular sieves
  3. temperatureThe reaction flask was cooled with an ice-water bath
  4. dissolutionto dissolve the oily product
  5. customproduce two layers
  6. concentrationThe heterogeneous brown mixture was concentrated under reduced pressure
  7. customto remove the organic solvents during which the product
  8. customprecipitated
  9. waitThe mixture was left
  10. waitto stand overnight in the refrigerator
  11. customThe precipitate was collected
  12. washwashed with ETOAc

Sources & evidence

ORD record
ord-97498c69733a4ae886bc5774198f54cf
Source dataset
uspto-grants-1998_04
Patent number
US05741715

Reaction notes

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