Hydrochloric Acid → HCID 68813721, compound

Participants

Reaction Steps

(2-(6-Benzenesulfonyl-1,2,3,4-tetrahydro-naphthalen-1-yloxy)-N-methyl-acetamide (0.7 g, 1.9 mmol) was dissolved in 25 mL of dry THF. Borane (10 mL of 1N THF solution) was added, and the reaction mixture was refluxed for three hours under nitrogen. The reaction mixture was cooled and 25 mL of 25% aqueous HCl was added. The reaction mixture was refluxed for 10 minutes, cooled, and solvent was removed under reduced pressure. The aqueous residue was basified by dropwise addition of 1N aqueous NaOH, and the aqueous mix was extracted three times with 50 mL of EtOAc. The combined organic layers were washed with water, brine, and dried over MgSO4. The residue was recrystallized from Et2O/MeOH/HCl to give 380 mg (1.1 mmol, 58%) of [2-(6-benzenesulfonyl-1,2,3,4-tetrahydro-naphthalen-1-yloxy)-ethyl]-methyl-amine hydrochloride. MS: 346 (M+H)+.

Provenance & Evidence