CC1C=CC(S(OCC2CC3C=CC(OC)=CC=3O2)(=O)=O)=CC=1.[N-]=[N+]=[N-].[Na+].[N:28]([CH2:31][CH:32]1[CH2:36][C:35]2[CH:37]=[CH:38][C:39]([O:41][CH3:42])=[CH:40][C:34]=2[O:33]1)=[N+]=[N-].[N-]=[N+]=[N-]>[Pd]>[CH3:42][O:41][C:39]1[CH:38]=[CH:37][C:35]2[CH2:36][CH:32]([CH2:31][NH2:28])[O:33][C:34]=2[CH:40]=1Treatment of (±)-(6-methoxy-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonate (1.00 g, 2.99 mmol) with sodium azide (0.78 g, 11.96 mmol) generally according to the procedure described for Intermediate 98 afforded (±)-2-(azidomethyl)-6-methoxy-2,3-dihydro-1-benzofuran. Treatment of the azide with palladium on carbon (0.06 g, 10 wt. %) generally according to the procedure described for Example 1 gave 0.442 g (69%) of (±)-1-(6-methoxy-2,3-dihydro-1-benzofuran-2-yl)methanamine as a white solid, hydrochloride salt. mp >220° C.; Anal. calcd. for C10H13NO2HCl: C, 55.69; H, 6.54; N, 6.49. Found: C, 55.29; H, 6.48; N, 6.38.
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