Trifluoroacetic acid → HCID 70471132, compound

HRID 745558Notes

Reaction equation

HRID 745558 reaction equation
[Cl-].[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH:10]=[C:11]2[CH:16]3[CH2:17][CH2:18][N+:13]([CH2:19][CH:20](O)[CH2:21][C:22]([O:24]C(C)(C)C)=[O:23])([CH2:14][CH2:15]3)[CH2:12]2)=[CH:5][CH:4]=1.FC(F)(F)C(O)=[O:33]>>[OH-:23].[C:22]([CH2:21][CH2:20][CH:19]([N+:13]12[CH2:18][CH2:17][CH:16]([CH2:15][CH2:14]1)[C:11](=[CH:10][CH2:9][C:6]1[CH:7]=[CH:8][C:3]([Cl:2])=[CH:4][CH:5]=1)[CH2:12]2)[OH:33])([OH:24])=[O:23]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 70470764HCID 70470764, compound

Product 1

HCID 70471132HCID 70471132, compound

Procedure

Stir 4.42 g (0.01 mole) of 3-[2-(4-chlorophenyl)ethylidene]-1-[3-((1,1-dimethylethoxy)carbonyl)-2-hydroxypropyl]-1-azoniabicyclo[2.2.2]octane chloride in 25 ml of trifluoroacetic acid. Follow the progress of the reaction by thin-layer chromatography on silica gel. When the reaction is complete (ca. 3-5 hr) remove the solvent in vacuo. Dissolve the residue in methanol/water. Stir the aqueous methanol solution with sufficient anion exchange resin (Biorad AG-1-X8, hydroxide form) to bring the pH of the solution to pH=9. Remove the resin by filtration and evaporate the solvent in vacuo at room temperature to provide the title compound.

Workup

  1. customthe progress of the reaction by thin-layer chromatography on silica gel
  2. custom(ca. 3-5 hr)
  3. customremove the solvent in vacuo
  4. dissolutionDissolve the residue in methanol/water
  5. customRemove the resin
  6. filtrationby filtration
  7. customevaporate the solvent in vacuo at room temperature

Sources & evidence

ORD record
ord-b7ef932be9e54c1b9d2114260c21bfcb
Source dataset
uspto-grants-1986_07
Patent number
US04599344

Reaction notes

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