[CH2:1]([N:8]([CH2:11][C@@H:12]1[O:17][C:16]2[C:18]([F:22])=[CH:19][CH:20]=[CH:21][C:15]=2[O:14][CH2:13]1)[CH2:9][CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li]CCCC.[CH3:28][S:29]C.[NH4+].[Cl-]>C1COCC1>[CH2:1]([N:8]([CH2:11][C@@H:12]1[O:17][C:16]2[C:18]([F:22])=[C:19]([S:29][CH3:28])[CH:20]=[CH:21][C:15]=2[O:14][CH2:13]1)[CH2:9][CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1A mixture of N-benzyl-N-{[(2S)-8-fluoro-2,3-dihydro-1,4-benzodioxin-2-yl]methyl}ethanamine (2.2 g, 7.3 mmol) and 2,2-tetramethylpiperidine (2.5 ml, 14.6 mmol) was added dropwise to n-BuLi (10 ml, 25 mmol) in THF (dry, 10 ml) under N2 at −75° C., followed by the addition of dimethylsulfide (1.32 ml, 14.6 mmol) in THF (dry, 10 ml). The mixture was stirred for 30 min at −75° C., and was then warmed to room temperature. NH4Cl (sat.) was added and the solution was extracted with EtOAc. The combined organic phases were washed with Na2SO3 (15%), brine, dried (Na2SO4) and evaporated to dryness. Flash column chromatography (isooctane/EtOAc) yielded the title compound (1.3 g). MS m/z (rel. intensity, 70 eV) 347 (2), 149 (12), 148 (100), 92 (7), 91 (92).
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