CC1C=CC(S(OCC2CC3C=CC=C(C4C=CC(OC)=CC=4)C=3O2)(=O)=O)=CC=1.[N-]=[N+]=[N-].[Na+].[N:34]([CH2:37][CH:38]1[CH2:42][C:41]2[CH:43]=[CH:44][CH:45]=[C:46]([C:47]3[CH:52]=[CH:51][C:50]([O:53][CH3:54])=[CH:49][CH:48]=3)[C:40]=2[O:39]1)=[N+]=[N-].[N-]=[N+]=[N-]>[Pd]>[CH3:54][O:53][C:50]1[CH:51]=[CH:52][C:47]([C:46]2[C:40]3[O:39][CH:38]([CH2:37][NH2:34])[CH2:42][C:41]=3[CH:43]=[CH:44][CH:45]=2)=[CH:48][CH:49]=1Treatment of (±)-[7-(4-methoxyphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl 4-methylbenzenesulfonate (2.1 g, 5.11 mmol) with sodium azide (1.33 g, 20.96 mmol) generally according to the procedure described for Intermediate 98 afforded (±)-2-(azidomethyl)-7-(4-methoxyphenyl)-2,3-dihydro-1-benzofuran. Treatment of the azide with palladium on carbon (0.125 g, 10 wt. %) generally according to the procedure described for Example 1 provided 0.860 g (58%) of (±)-1-[7-(4-methoxyphenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine as a white solid, hydrochloride salt. mp 176-178° C.; Anal. calcd. for C16H17NO2HCl: C, 65.86; H, 6.22; N, 4.80. Found: C, 65.02; H, 6.13; N, 4.57.
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