Hydrochloric Acid → (+/-)-(5-Chloro-2,3-dihydronaphtho[1,2-b]furan-2-yl)methyl azide

Participants

Reaction Steps

Treatment of (±)-3-[1-(benzyloxy)-4-chloro-2-naphthyl]-2-hydroxypropyl 4-methylbenzenesulfonate (4.6 g, 9.26 mmol) with palladium on carbon (5 wt. %, 0.50 g) and hydrogen chloride in isopropanol (4.0 M, 4.0 mL) generally according to the procedure described for Intermediate 4 provided (±)-3-(4-chloro-1-hydroxy-2-naphthyl)-2-hydroxypropyl 4-methylbenzenesulfonate. Treatment of the phenyl with triphenylphosphine (3.5 g, 13.3 mmol) followed by diisopropylazodicarboxylate (2.69 g, 13.3 mmol) generally according to the procedure described for Intermediate 5 afforded (±)-(5-chloro-2,3-dihydronaphtho[1,2-b]furan-2-yl)methyl 4-methylbenzenesulfonate as a colorless oil. Treatment of the tosylate with sodium azide (1.1 g, 16.4 mmol) generally according to the procedure described for Intermediate 24 gave (±)-(5-chloro-2,3-dihydronaphtho[1,2-b]furan-2-yl)methyl azide as a pale brown oil. Treatment of the azide with sulfided platinum on carbon (5 wt. %, 0.15 g) generally according to the procedure described for Example 2 provided 1.07 g (43%) of (±)-1-(5-chloro-2,3-dihydronaphtho[1,2-b]furan-2-yl)methanamine as a white solid, hydrochloride salt. mp 269-271° C.; Anal. calcd. for C13H12ClNOHCl.0.8H2O: C, 54.87; H, 5.17; N, 4.92. Found: C, 54.68; H, 4.78; N, 4.79.

Provenance & Evidence