Tetrahydrofuran → N-(Bicyclo[2.2.1]hept-5-en-2-ylmethyl)-1-propanesulfonamide

Temperature

0 °C

Into a dry 1 lit. round bottom flask equipped with a magnetic stirrer, condenser and an addition funnel was added 500 ml of dry distilled tetrahydrofuran, 63 g (0.51 moles) of norbornyl amine and 125 ml (0.41 moles) of triethylamine. The reaction mixture was cooled to 0° C. To the mixture was added via the additional funnel 65 g (0.495 moles) of propanesulfonyl chloride and the reaction mixture was stirred overnight. The reaction mixture was filtered to remove the triethylammonium hydrochloride salt and the filtrate was rotovaped to remove tetrahydrofuran, resulting in an solid. The solid was dissolved in diethylether, and the resulting solution was extracted several times with deionized water. After treating with decolorizing carbon and drying over anhydrous sodium sulfate, the solution was filtered and the solvent was removed by rotary evaporation. The solid product was recrystallized from hexane's and dried under reduced pressure to yield 85%, mp 51-52° C. The product was identified by 1H and 13C NMR and IR spectroscopy.

1. customInto a dry 1 lit. round bottom flask equipped with a magnetic stirrer, condenser and an addition funnel
2. additionwas added 500 ml
3. customof dry
4. filtrationThe reaction mixture was filtered
5. customto remove the triethylammonium hydrochloride salt
6. customto remove tetrahydrofuran
7. customresulting in an solid
8. extractionthe resulting solution was extracted several times with deionized water
9. additionAfter treating with decolorizing carbon
10. dry with materialdrying over anhydrous sodium sulfate
11. filtrationthe solution was filtered
12. customthe solvent was removed by rotary evaporation
13. customThe solid product was recrystallized from hexane's
14. customdried under reduced pressure
15. customto yield 85%, mp 51-52° C

ORD record

ord-718884642f9b4586977121440a6a704e

Source dataset

uspto-grants-2001_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06235849B1