The esterification of 5,8-dihydro-1-naphthol (I) with acetic anhydride gives the corresponding acetate (II), which is oxidized with silver acetate and I2 in acetic acid to yield 2,3-cis-1,2,3,4-tetrahydro-2,3,5-naphthalenetriol (III). The treatment of this product with sodium methylate and epichlorhydrin (A) in methanol gives 2,3-cis-1,2,3,4-tetrahydro-5-(2,3-epoxypropoxy)-2,3-naphthalenediol (IV), which is finally treated with tertbutylamine (B) in chloroform-methanol.
By reaction of 5,8-dihydro-1-(2,3-epoxypropoxy)naphthalene (V) with tertbutylamine (B) to give 5,8-dihydro-1-[2-hydroxy-3-(tertbutylamino)propoxy]naphthalene (VI), followed by oxidation of the double bond with silver acetate and I2 in acetic acid.