Hydrochloric Acid → HCID 178445741, compound

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Reaction Steps

To a solution of 2-methyl-propane-2-sulfinic acid {3-[6-(trans-4-tert-butyl-cyclohexyloxy)-5-trifluoromethyl-naphthalen-2-yl]-oxetan-3-yl}-amide (332 mg, 0.632 mmol) in methylene chloride (7 mL, 100 mmol) was added 2.0 M of hydrogen chloride in ether (0.632 mL, 1.26 mmol) and stirred for 10 min. A precipitate formed and cyclohexane was added to dilute the mixture. After removal of solvent, the residue was dissolved in methylene chloride, 1M aq. NH4OH was added, the extracted organic layer was dried and subjected to silica gel chromatography with MeOH/CH2Cl2 (20-40%) to give 3-(6-(trans-4-tert-butylcyclohexyloxy)-5-(trifluoromethyl)naphthalen-2-yl) oxetan-3-amine as a solid (213.7 mg, 80%). LCMS: Rf=1.67 min 405.20 ([M−16]). 1H NMR (400 MHz, CHLOROFORM-d) δ=8.27 (d, J=9.3 Hz, 1H), 7.93 (d, J=9.2 Hz, 1H), 7.91 (d, J=1.9 Hz, 1H), 7.81 (dd, J=2.1, 9.3 Hz, 1H), 7.33 (d, J=9.2 Hz, 1H), 5.06 (d, J=6.5 Hz, 2H), 4.82 (d, J=6.5 Hz, 2H), 4.38-4.24 (m, 1H), 2.20 (d, J=12.4 Hz, 2H), 1.93-1.82 (m, 2H), 1.55 (br. s., 2H), 1.41-1.09 (m, 5H), 0.89 (s, 9H).

Provenance & Evidence