C[S-].[Na+].C[O:5][C:6]1[CH:7]=[C:8]([C:12]2([CH2:18][N:19]([CH3:21])[CH3:20])[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[CH:9]=[CH:10][CH:11]=1.Br.C([O-])(O)=O.[Na+]>CN(C=O)C.O>[CH3:21][N:19]([CH2:18][C:12]1([C:8]2[CH:7]=[C:6]([OH:5])[CH:11]=[CH:10][CH:9]=2)[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)[CH3:20]
To a suspension of Sodium thiomethoxide (0.42 g, 6 mmol) in DMF (1.2 mL) was added N-{[4-(3-methoxyphenyl)tetrahydro-pyran-4-yl]methyl}-N,N-dimethylamine (0.3 g, 1.2 mmol) and the resulting mixture was heated to 65° C. for 7 h, allowed to cool to ambient temperature and quenched with saturated aqueous NH4Cl (6 mL). The mixture was extracted with DCM, dried over Na2SO4, filtered and concentrated in vacuo to provide 0.25 g of crude product. A mixture of the crude and HBr (3 mL) was heated to reflux for 1 h. After cooling, water was added to quench the reaction and the mixture was basified with NaHCO3 and extracted with DCM. The organic extracts were dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography (DCM/MeOH (10% NH3)) to provide 3-{4-[(dimethylamino)methyl]tetrahydro-pyran-4-yl}phenol (0.100 g, 35.5%).
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