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A solution of methanesulfonic acid 2-(6-benzenesulfonyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-ethyl ester (1.12 g, 2.84 mmol) in thy DMF (25 mL) was stirred under argon at room temperature. Solid potassium iodide (0.25 g) and sodium azide (0.185 g, 2.84 mmol) were added, and the reaction mixture was allowed to stir for 48 hours. The reaction mixture was poured into 500 mL of water, and the aqueous mixture was extracted four times with 150 mL of EtOAc. The combined organic layers were washed with water, brine, dried (MgSO4), and evaporated under reduced pressure to give an oil that was purified by eluting through silica gel with hexanes:EtOAc (3:2). After solvent removal, the resulting oil was dissolved in dry THF, cooled to 0° C., and 5.68 mL of lithium aluminum hydride in THF (5.68 mmol) was added dropwise via syringe to the stirring reaction mixture. The reaction mixture was allowed to warm to room temperature (about 30 minutes) and was quenched by addition to 250 mL of water. The aqueous solution was extracted twice with 250 mL of EtOAc, and the combined organic layers were washed with water, brine, dried (MgSO4), and evaporated under reduced pressure to give an oil. The oil was dissolved in MeOH, 2 mL of 2M HCl in Et2O) was added, and the solution was gently warmed, then cooled. The resulting residue was recrystallized from MeOH/Et2O to afford 0.17 g (0.483 mmol, 17%) of 2-(6-benzenesulfonyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-ethylamine hydrochloride salt. MS: 316 (M+H)+.

1. extractionthe aqueous mixture was extracted four times with 150 mL of EtOAc
2. washThe combined organic layers were washed with water, brine
3. dry with materialdried (MgSO4)
4. customevaporated under reduced pressure
5. customto give an oil that
6. customwas purified
7. washby eluting through silica gel with hexanes:EtOAc (3:2)
8. customAfter solvent removal
9. dissolutionthe resulting oil was dissolved in dry THF
10. temperatureto warm to room temperature (about 30 minutes)
11. customwas quenched by addition to 250 mL of water
12. extractionThe aqueous solution was extracted twice with 250 mL of EtOAc
13. washthe combined organic layers were washed with water, brine
14. dry with materialdried (MgSO4)
15. customevaporated under reduced pressure
16. customto give an oil
17. temperaturethe solution was gently warmed
18. temperaturecooled
19. customThe resulting residue was recrystallized from MeOH/Et2O