Itameline, RU-47213

1(2H)-吡啶羧酸,3,6-二氢-5-[(甲氧基亚基)甲基]-,4-氯苯酯Chemical Name: (E)-1-(4-Chlorophenoxycarbonyl)-1,2,5,6-tetrahydropyridine-3-carboxaldehyde O-methyloxime; (E)-3-[(Methoxyimino)methyl]-1,2,5,6-tetrahydropyridine-1-carboxylic acid 4-chlorophenyl ester
CAS No. 121750-57-0
项目整合开发状态: Phase I
项目研究机构: Aventis Pharma (Originator)
合成路线:Pyridine-3-carboxaldehyde O-methyloxime (I) is prepared either by methylation of 3-pyridinealdoxime sodium salt or by condensation of 3-pyridinecarboxaldehyde with methoxylamine in water.Quaternization of (I) with ethyl iodide gives 3-(methoxyiminomethyl)-1-ethylpyridinium iodide (II),which is reduced by means of sodium borohydride in methanol to 1-ethyl-1,2,5,6-tetrahydropyridine-3-carboxaldehyde O-methyloxime (III).Cleavage of the ethyl group is obtained by reaction with 4-chlorophenylchloroformate in refluxing dichloroethane to yield RU 47213.Ru 47213 is obtained as pure (E)-isomer.Under UV irradiation in toluene it is partially converted into the sterically unfavored (Z)-isomer.