Hydrochloric Acid → HCID 178445740, compound

Participants

Reaction Steps

To a solution of 2-methyl-propane-2-sulfinic acid {3-[6-(4-tert-butyl-cyclohexyloxy)-naphthalen-2-yl]-oxetan-3-yl}-amide (86 mg, 0.19 mmol) in methylene chloride (2 mL, 30 mmol) was added 2.0 M of hydrogen chloride in ether (0.188 mL, 0.376 mmol) and was stirred 10 min. A precipitate formed and cyclohexane was added to dilute the mixture. After removal of solvent, the residue was dissolved in methylene chloride, 1 M aq. NH4OH was added and the extracted organic layer was dried and chromatographed with MeOH/CH2Cl2 (20-40%) to give 3-(6-(trans-4-tert-butylcyclohexyloxy)naphthalen-2-yl)oxetan-3-amine as a solid (44.8 mg, 67%). LCMS: Rf=1.55 min 337.20 ([M−16]). 1H NMR (400 MHz, CHLOROFORM-d) δ=7.84 (d, J=1.4 Hz, 1H), 7.81-7.70 (m, 2H), 7.66 (d, J=1.9 Hz, 1H), 7.22-7.12 (m, 2H), 5.09 (d, J=6.7 Hz, 2H), 4.81 (d, J=6.7 Hz, 2H), 4.29 (tt, J=4.2, 10.8 Hz, 1H), 2.29 (d, J=13.2 Hz, 2H), 1.91 (d, J=12.5 Hz, 2H), 1.56-1.39 (m, 2H), 1.29-1.02 (m, 3H), 0.91 (s, 9H).

Provenance & Evidence