Diethyl Ether → 1a,2,7,7a-Tetrahydronaphtho[2,3-b]oxiren-3-ol

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Reaction Steps

Alternatively, the 2,3-trans-1,2,3,4-tetrahydro-5-[2-hydroxy-3-(alkylamino)propoxy]-2,3-naphthalenediol of formula II can be prepared from a 5,8-dihydro-1-naphthol of formula IX by mixing a cooled solution (temperature less than about 30° C.) of 5,8-dihydro-1-naphthol in ethyl acetate with m-chloroperbenzoic acid and mixing the resulting slurry with a mixture of ethyl ether and aqueous sodium bicarbonate, to form a 5,6,7,8-tetrahydro-6,7-epoxy-1-naphthol having the formula ##STR17## A 5,6,7,8-tetrahydro-6,7-epoxy-1-naphthol of formula XVI in tetrahydrofuran can be reacted with aqueous perchloric acid at a temperature within the range of from about 0° to about 60° C., to form a trans-5,6,7,8-tetrahydro-1,6,7-naphthalenetriol or formula XI which can be converted to the corresponding 2,3-trans-1,2,3,4-tetrahydro-5-[2,3-(epoxy)propoxy]-2,3-naphthanediol of formula XII, which in turn can be converted to the corresponding 2,3-trans-1,2,3,4-tetrahydro-5-[2-hydroxy-3-(alkylamino)propoxy]-2,3-naphthalenediol of formula II using the procedures described above.

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