[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]1[CH2:15][OH:16].[CH3:17][S:18](Cl)(=[O:20])=[O:19].CNC1C=CC=C(NC)N=1.CCN(CC)CC>[Cl-].[Na+].O.O.ClCCl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]1[CH2:15][O:16][S:18]([CH3:17])(=[O:20])=[O:19]Combine [2-(2-methoxy-phenyl)-cyclohexyl]-methanol (0.725 g, 3.29 mmol), methanesulfonyl chloride (0.415 g, 3.62 mmol), 2,6-dimethylaminopyridine (80.0 mg, 0.66 mmol), Et3N (1.0 mL, 7.24 mmol), and dichloromethane (30.0 mL) at 0° C. After 20 min stir at room temperature under nitrogen. Reaction stirred for 18 hours then add water and brine. Separate layers and dry over anhydrous sodium sulfate. Concentrate and flash chromatography using 5 to 30% ethyl acetate/hexanes to yield the titled compound (0.810 g, 83%). TLC Rf=0.25 in 30% ethyl acetate/hexanes. 1H NMR (CDCl3): 7.2 (m, 1H), 7.1 (m, 1H), 6.9 (m, 2H), 4.3 (t, 1H, J=10.0 Hz), 3.9 (m, 4H), 3.3 (m, 1H), 2.8 (s, 3H), 2.6 (m, 1H), 1.8 (m, 6H), 1.5 (m, 2H).
Wird geladen…
