| 摘要 |
<p>PURPOSE:To obtain a new intermediate compound, composed of (1RS, 2RS, 4RS)-4-amino-2-(3-pyridyl)-1-cyclohexanols and derivatives thereof and useful as a synthetic intermediate, etc., for epibatidine useful as an analgesic agent. CONSTITUTION:3-Bromo-6-methoxypyridine is treated with t-butyl-lithium in dry THF at -78 deg.C and the resultant compound then reacts with 4-acetoxy-2- cyclohexenone in the presence of copper iodide and boron trifluoride-diethyl ether to provide a cvclohexanone derivative of formula 1 (R<1> is 1-4C alkyl or benzyl; R<3> is 1-4C alkyl, 2-5C aliphatic acyl, etc.), which is further treated with sodium cyanoborohydride. The produced amino group is protected to afford a new compound of formula II (Y is protecting group), which is then hydrolyzed to provide a new cyclohexanol compound of formula III. Furthermore, the resultant compound is then sulfonylated to afford a new compound of formula IV, which reacts with phosphorus oxychloride or phosgene to provide the objective intermediate compound of formula V.</p> |
