Sodium Azide → (+/-)-1-(5-Chloro-7-methoxy-2,3-dihydro-1-benzofuran-2-yl)methanamine

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Reaction Steps

Treatment of (±)-(5-chloro-7-methoxy-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonate (1.10 g, 2.98 mmol) with sodium azide (1.5 g, 23.1 mmol) generally according to the procedure described for Intermediate 98 provided (±)-2-(azidomethyl)-5-chloro-7-methoxy-2,3-dihydro-1-benzofuran. Treatment of the azide with sulfided platinum on carbon (0.080 g, 5 wt. %) generally according to the procedure described for Example 1 afforded 0.415 g (56%) of (±)-1-(5-chloro-7-methoxy-2,3-dihydro-1-benzofuran-2-yl)methanamine as a white solid, hydrochloride salt. mp 195-198° C.; Anal. calcd. for C10H12ClNO2HCl: C, 48.02; H, 5.24; N, 5.6. Found: C, 46.41; H, 5.09; N, 5.31.

Provenance & Evidence