FC(F)(F)C(O)=O.C(OC(=O)[NH:14][CH:15]([CH:24]1[CH2:29][CH2:28][CH:27]([OH:30])[CH2:26][CH2:25]1)[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)(C)(C)C.Cl.O>ClCCl.C(#N)C>[NH2:14][CH:15]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)[CH:24]1[CH2:29][CH2:28][CH:27]([OH:30])[CH2:26][CH2:25]1Trifluoroacetic acid (0.31 mL) was added to a solution of [(4-hydroxy-cyclohexyl)-(4-methoxy-phenyl)-methyl]-carbamic acid tert-butyl ester (34, 101 mg) in dichloromethane (6 mL). After stirring for 2 hours, 2M hydrochloric acid (3 mL) was added. Evaporation gave crude product as a colourless solid. Water and acetonitrile were added and the mixture was concentrated and then freeze dried to give 83 mg of 4-[amino-(4-methoxy-phenyl)-methyl]-cyclohexanol (35) as the hydrochloride salt. Rt=0.71 min (Method 5). Detected mass: 219.2 (M—NH2+).
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