Sodium Iodide → [2-(6-Benzenesulfonyl-1,2,3,4-tetrahydro-naphthalen-1-ylamino)-ethyl]-methyl-carbamic acid tert-butyl ester

Participants

Reaction Steps

6-Benzenesulfonyl-1-chloro-1,2,3,4-tetrahydro-naphthalene (0.6 g, 1.95 mmol), (2-Amino-ethyl)-methyl-carbamic acid tert-butyl ester (0.512 g, 2.925 mmol), sodium iodide (0.1 g) and potassium carbonate (0.5 g) were added to 50 mL of acetonitrile, and the reaction mixture was refluxed for 120 hours. The reaction mixture was cooled and diluted with 200 mL of water. The aqueous mix was extracted twice with 200 mL of EtOAc, and the combined organic layers were washed with water, brine, and dried over MgSO4. Solvent was removed under reduced pressure, and the resulting oil was eluted through silica gel (medium pressure chromatography) eluting with EtOAc/Hexanes 20%/80%. Removal of solvent under reduced pressure afforded 0.4 g (0.9 mmol, 46%) of [2-(6-benzenesulfonyl-1,2,3,4-tetrahydro-naphthalen-1-ylamino)-ethyl]-methyl-carbamic acid tert-butyl ester as an oil. MS: 446 (M+H)+.

Provenance & Evidence