CC1C=CC(S(OCC2CC3C=CC=C(C4C=CC(F)=CC=4)C=3O2)(=O)=O)=CC=1.[N-]=[N+]=[N-].[Na+].[N:33]([CH2:36][CH:37]1[CH2:41][C:40]2[CH:42]=[CH:43][CH:44]=[C:45]([C:46]3[CH:51]=[CH:50][C:49]([F:52])=[CH:48][CH:47]=3)[C:39]=2[O:38]1)=[N+]=[N-].[N-]=[N+]=[N-]>[Pd]>[F:52][C:49]1[CH:48]=[CH:47][C:46]([C:45]2[C:39]3[O:38][CH:37]([CH2:36][NH2:33])[CH2:41][C:40]=3[CH:42]=[CH:43][CH:44]=2)=[CH:51][CH:50]=1Treatment of (±)-[7-(4-fluorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl 4-methylbenzenesulfonate (1.1 g, 3.01 mmol) with sodium azide (0.784 g, 12.04 mmol) generally according to the procedure described for Intermediate 98 afforded (±)-2-(azidomethyl)-7-(4-fluorophenyl)-2,3-dihydro-1-benzofuran. Treatment of the azide with palladium on carbon (0.074 g, 10 wt. %) generally according to the procedure described for Example 1 provided 0.542 g (64%) of (±)-1-[7-(4-fluorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine as a white solid, hydrochloride salt. mp 237-240° C.; Anal. calcd. for C15H14FNOHCl: C, 64.4; H, 5.4; N, 5.01. Found: C, 64.26; H, 5.33; N, 4.85.
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