Triethylamine → HCID 22591345, compound

HRID 22960Notes

Reaction equation

HRID 22960 reaction equation
[CH2:1](N(CC)CC)[CH3:2].CS([Cl:12])(=O)=O.C(OC([N:20]1[CH2:28][C:27]2[C:22](=[CH:23][CH:24]=[C:25]([CH2:29][OH:30])[CH:26]=2)[CH2:21]1)=O)(C)(C)C.Cl.O1CCOCC1>O1CCOCC1.O.O1CCCC1>[ClH:12].[CH2:1]([O:30][CH2:29][C:25]1[CH:26]=[C:27]2[C:22](=[CH:23][CH:24]=1)[CH2:21][NH:20][CH2:28]2)[CH3:2]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 204431481,4-Dioxane hydrochlorideHCID 22591344tert-butyl 5-(hydroxymethyl)-2,3-dihydro-1H-isoindole-2-carboxylate

Product 1

HCID 22591345HCID 22591345, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Procedure

0.84 ml of triethylamine and 0.37 ml of methanesulfonyl chloride were added to 10 ml of a tetrahydrofuran solution containing 0.99 g of 2-tert-butoxycarbonyl-5-(hydroxylmethyl)isoindoline under ice-cooling, and the mixture was stirred under ice-cooling for 1 hour. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. After the extract was dried over sodium sulfate, the solvent was removed under reduced pressure. To the residue were added 20 ml of ethanol and 1.02 ml of diisopropylethylamine, and the mixture was refluxed for 30 minutes. The reaction mixture was concentrated under reduced pressure, and ethyl acetate and an aqueous 5% hydrochloric acid solution were added to the residue, followed by the extraction. After the extract was dried over sodium sulfate, the solvent was removed under reduced pressure. The residue was purified by silica gel chromatography (solvent: hexane-ethyl acetate=4:1) to obtain an oily product. This oily product was dissolved in 5 ml of dioxane, then, 8 ml of 4N hydrochloric acid-dioxane was added thereto, and the mixture was stirred at room temperature. The precipitates precipitated by addition of 20 ml of ether were collected by filtration and washed with ether to obtain 5-(ethoxymethyl)isoindoline.hydrochloride.

Workup

  1. temperaturecooling
  2. temperaturecooling for 1 hour
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialAfter the extract was dried over sodium sulfate
  5. customthe solvent was removed under reduced pressure
  6. additionTo the residue were added 20 ml of ethanol and 1.02 ml of diisopropylethylamine
  7. temperaturethe mixture was refluxed for 30 minutes
  8. concentrationThe reaction mixture was concentrated under reduced pressure, and ethyl acetate
  9. additionan aqueous 5% hydrochloric acid solution were added to the residue
  10. extractionfollowed by the extraction
  11. dry with materialAfter the extract was dried over sodium sulfate
  12. customthe solvent was removed under reduced pressure
  13. customThe residue was purified by silica gel chromatography (solvent: hexane-ethyl acetate=4:1)
  14. customto obtain an oily product
  15. stirringthe mixture was stirred at room temperature
  16. customThe precipitates precipitated by addition of 20 ml of ether
  17. filtrationwere collected by filtration
  18. washwashed with ether

Sources & evidence

ORD record
ord-94c46e1b843e4b5090f6c39860922130
Source dataset
uspto-grants-2005_02
Patent number
US06849622B2

Reaction notes

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