(-)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(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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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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