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| Ezetimibe的合成 | |
| 引用本文： | 黄伟,岑均达. Ezetimibe的合成[J]. 中国医药工业杂志, 2006, 37(6): 364-366 |
| 作者姓名： | 黄伟 岑均达 |
| 作者单位： | 上海医药工业研究院,上海,200437 |
| 摘 要： | (4S)-3-[(5S)-5-(4-氟苯基)-5-羟基-1-氧代戊基]-4-苯基-2-(?)唑烷酮与4-(4-氟苯基亚氨基)甲酚缩合后再经环合、脱硅烷保护得ezetimibe。前一中间体可以氟苯为原料,与戊二酸酐经付-克反应得到的5-(4-氟苯基)-5-氧代戊酸,与特戊酰氯缩合得到混合酸酐,再与(4S)-4-苯基-2-(?)唑烷酮缩合得(4S)-3-[5-(4-氟苯基)-1,5-二氧代戊基]-4-苯基-2-(?)唑烷酮,经(3αR)-1-甲基-3,3-二苯基-1H,3H-四氢吡咯并[1,2-c][1.3.2](?)唑硼烷[(R)-MeCBS]／BH3·S(CH3)2催化还原制得。总收率24％。 |
| 关 键 词： | 依替米贝 胆固醇吸收抑制剂 合成 |
| 文章编号： | 1001-8255（2006）06-0364-03 |
| 收稿时间： | 2006-03-14 |
| 修稿时间： | 2006-03-14 |
Synthesis of Ezetimibe |
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| HUANG Wei,CEN Jun-Da. Synthesis of Ezetimibe[J]. , 2006, 37(6): 364-366 | |
| Authors: | HUANG Wei CEN Jun-Da |
| Abstract: | Ezetimibe was synthesized from (45)-3-[(5S)-5-(4-fluorophenyl) -5-hydroxy-1-oxopentyl] -4-phenyl-2-oxazolidinone and 4-[[(4-fluorophenyl) imino] methyl] phenol. The former key intermediate was prepared from fluorobenzene by Friedel-Crafts acylation with glutaric anhydride, followed by successive condensations with pivaloyl chloride and (4S) -4-phenyl-2-oxazolidinone and then underwent catalytic reduction by (R) -MeCBS/borane-methyl sulfide. The overall yield was 24%. |
| Keywords: | ezetimibe hypocholesterolemic agent synthesis |
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