Sodium Azide → (+/-)-2-(Azidomethyl)-2,3,6,7,8,9-hexahydronaphtho[1,2-b]furan

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Reaction Steps

Treatment of (±)-2,3,6,7,8,9-hexahydronaphtho[1,2-b]furan-2-ylmethyl 4-methylbenzenesulfonate (2.05 g, 5.72 mmol) with sodium azide (0.929 g, 14.30 mmol) generally according to the procedure described for Intermediate 24 gave (±)-2-(azidomethyl)-2,3,6,7,8,9-hexahydronaphtho[1,2-b]furan. Treatment of the azide with palladium on carbon (10 wt. %, 0.094 g) generally according to the procedure described for Example 2 afforded 0.917 g (67%) of (±)-1-(2,3,6,7,8,9-hexahydronaphtho[1,2-b]furan-2-yl)methanamine as a white solid, hydrochloride salt. mp>220° C. (dec.); Anal. calcd. for C13H17NOHCl.0.1H2O: C, 64.15; H, 7.50; N, 5.75. Found: C, 64.41; H, 7.64; N, 5.67.

Provenance & Evidence