CC1C=CC(S(OCC2CC3C(F)=CC=C(C4C=CC=CC=4C)C=3O2)(=O)=O)=CC=1.[N-]=[N+]=[N-].[Na+].[N:34]([CH2:37][CH:38]1[CH2:42][C:41]2[C:43]([F:54])=[CH:44][CH:45]=[C:46]([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=3[CH3:53])[C:40]=2[O:39]1)=[N+]=[N-].[N-]=[N+]=[N-]>[Pd]>[F:54][C:43]1[C:41]2[CH2:42][CH:38]([CH2:37][NH2:34])[O:39][C:40]=2[C:46]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=2[CH3:53])=[CH:45][CH:44]=1Treatment of (±)-[4-fluoro-7-(2-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl 4-methylbenzenesulfonate (1.38 g, 3.35 mmol) with sodium azide (0.87 g, 13.38 mmol) generally according to the procedure described for Intermediate 98 afforded (±)-2-(azidomethyl)-4-fluoro-7-(2-methylphenyl)-2,3-dihydro-1-benzofuran. Treatment of the azide with palladium on carbon (0.083 g, 10 wt. %) generally according to the procedure described for Example 1 provided 0.561 g (57%) of (±)-1-[4-fluoro-7-(2-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine as a white solid, hydrochloride salt. mp 228-231° C.; Anal. calcd. for C16H16FNOHCl: C, 65.42; H, 5.83; N, 4.77. Found: C, 66.01; H, 5.88; N, 4.51.
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