Synthesis of trans-4-aryl-3-(3-chloropropyl)azetidin-2-ones and their transformation into trans- and cis-2-arylpiperidine-3-carboxylates
- 作者：Matthias D'hooghe ; Yves Dejaegher ; Norbert De Kimpe
- 关键词：Rural electric coops ; Quadratic cost models ; Economies of vertical integration
- 刊名：Tetrahedron
- 出版年：2008
- 期刊代码：107_00404020
- 类别：ch
- 出版时间：12 May 2008
- 卷：64
- 期：20
- 页码：4575-4584
- 文件大小：349 K
摘要
Treatment of arylmethylideneamines with 5-chloropentanoyl chloride in benzene in the presence of 2,6-lutidine afforded novel trans-4-aryl-3-(3-chloropropyl)azetidin-2-ones in good yields. The latter 3-(3-chloropropyl)-β-lactams were transformed selectively into trans-methyl 1-alkyl-2-arylpiperidine-3-carboxylates in high yields and purity upon subsequent treatment with hydrogen chloride in methanol and triethylamine in dichloromethane. These trans-1-alkyl-2-arylpiperidine-3-carboxylates were easily converted into either their cis-isomers upon treatment with hydrazine monohydrate in methanol, or into the corresponding piperidine-1,3-dicarboxylates by reaction with alkyl chloroformates in benzene. Finally, 3-(3-chloropropyl)-1-(4-methoxybenzyl)-4-phenylazetidin-2-one was transformed into the corresponding trans-1-tert-butoxycarbonyl-3-(4-methoxybenzylcarbamoyl)piperidine via a three-step sequence in a good overall yield.