反应详情

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.

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