| （-）反式-4R（4-氟苯基）-3S-羟甲基-1-甲基哌啶的合成 |
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| 引用本文： | 王一军,从顺宝. （-）反式-4R（4-氟苯基）-3S-羟甲基-1-甲基哌啶的合成[J]. 化工中间体, 2007, 0(11): 8-12,28 |
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| 作者姓名： | 王一军 从顺宝 |
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| 作者单位： | [1]浙江捷马化工有限公司,浙江杭州310003; [2]上虞颖泰化工有限公司,浙江绍兴312000 |
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| 摘 要： | 亚磷酸三乙酯与氯乙酸乙酯进行缩合、重排、脱氯乙烷合成磷酸酯，再与对氟苯甲醛经Knoevenagel反应合成肉桂酸酯，肉桂酸酯与丙二酸二乙酯胺解合成的N-甲胺基羰基乙酸乙酯环合得到哌啶二酮。环化物用硼氢化钾复合还原剂还原得±4-（4-氟苯基）-3-羟甲基-1-甲基哌啶，对混旋体进行手性拆分得目标产物（4R，3S）-4-氟苯基-3-羟甲基-1-甲基哌啶。选择自制酸载硅胶催化剂catl#、醋酸-乙二胺催化剂cat2#、复合相转移催化剂cat3#为各步催化剂，反应收率分别为89．1％，96．3％，86．5％，76．3名，87．2％，43．7％，总收率24.3％，比旋光度-36～-38°，纯度大于99％。
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| 关 键 词： | 亚磷酸三乙酯 氯乙酸乙酯 N-甲胺基羰基乙酸乙酯 4-氟肉桂酸乙酯 |
| 文章编号： | 1006-253x（2007）11-008-5 |
| 收稿时间： | 2007-04-13 |
Synthesis of (-)-Trans-4R-(4''''-fluorophenyl)-3S-hydroxymethyl-1-methylpiperidine |
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| WANG Yi-jun,CONG Shun-bao. Synthesis of (-)-Trans-4R-(4''''-fluorophenyl)-3S-hydroxymethyl-1-methylpiperidine[J]. , 2007, 0(11): 8-12,28 |
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| Authors: | WANG Yi-jun CONG Shun-bao |
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| Affiliation: | WANG Yi-jun,CONG Shun-bao (1.Zhejiang JMC Chemical Co., Ltd., Hangzhou 310003, Zhejiang, China; 2.Shangyu Yingtai Chemical Co., Ltd., Shaoxing 312000, Zhefiang, China) |
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| Abstract: | The preparation of （-）trans-4R-（4＇-fluorophenyl）-3S-hydroxymethyl-l-methylpiperidine from triethyl phosphite, diethyl malonate,4-fluorobenzaldehyde,ethyl chloroacetate, under the condition of existing cat1#,cat2#, cat3# catalysts was presented. The effect of catalyst 1#,2#,3#, reduction agent, chiral resolving agent and pH control was discussed.The overall yield is 24.27%, the optical rotation is -36～-38°, and the HPLC purity is over 99%. |
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| Keywords: | triethyl phosphate diethyl malonate ethyl chloroacetate 4-fluorobenzaldehyde ethyl 4- florocinnamate 4R-（4＇-fluorophenyl）-3S-hydroxymethyl-l-methylpiperidine chiral resolving agent 4- （4-flurophenyl）-3-ethoxycarbonyl- 1-methyl piperdine-2,6-dione |
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