Boron tribromide → (1R*,2R*)-1,2,3,4-tetrahydro-6-hydroxy-2-(4-hydroxyphenyl)-1-(1H-imidazol-1-ylmethyl)naphthalene

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Reaction Steps

A solution of (1R*,2R*)-1,2,3,4-tetrahydro-1-(1H-imidazol-1-ylmethyl)-6-methoxy-2-(4-methoxyphenyl)naphthalene, (prepared as described in Example 1), in dichloromethane (20 ml) was stirred in an argon atmosphere and cooled in an acetone/solid carbon dioxide bath while a 1M solution of boron tribromide was added dropwise over 5 minutes. The mixture was kept at -20° for 48 h, then poured into a mixture of saturated sodium bicaronate solution (30 ml) and stirred vigorously for 2 h. The solid thus obtained was filtered off, washed with water (100 ml) then dichloromethane (100 ml) and dried in a desiccator under reduced pressure to give (1R*,2R*)-1,2,3,4-tetrahydro-6-hydroxy-2-(4-hydroxyphenyl)-1-(1H-imidazol-1-ylmethyl)naphthalene, m.p. 238°.

Provenance & Evidence