2-Ethoxy-piperidine-1-carboxylic acid benzyl ester | 106412-43-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-Ethoxy-piperidine-1-carboxylic acid benzyl ester
• 英文别名: Benzyl 2-ethoxypiperidine-1-carboxylate
• CAS: 106412-43-5
• 化学式: C₁₅H₂₁NO₃
• 分子量: 263.337
• InChiKey: KAWWQBFXHLWWEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Ethoxy-piperidine-1-carboxylic acid benzyl ester 在 palladium dihydroxide 氢气 、 三乙基硅基三氟甲磺酸酯 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 哌醋右甲酯
  参考文献：
  名称：

  Short Synthesis of Methylphenidate and Itsp-Methoxy Derivative

  摘要：

  A short method for the preparation of racemic threo- and erythro-methylphenidate derivatives is described. Condensation between a-ethoxy carbamate 1 and silyl ketene acetals 2a-b in the presence of TESOTf (20 mol%) afforded a 1.5:1 mixture of carbamates 3a-b/4a-b. Hydrogenolysis in EtOH followed by treatment with 3N HCl/MeOH afforded the corresponding hydrochlorides 7a-b/8a-b in good yields.

  DOI：

  10.1080/00397910008087153
• 作为产物：
  描述：

  4-氯丁醛缩二乙醇 在 lithium aluminium tetrahydride 、 对甲苯磺酸 、 N,N-二异丙基乙胺 、 potassium iodide 作用下， 以 乙醚 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 28.0h， 生成 2-Ethoxy-piperidine-1-carboxylic acid benzyl ester
  参考文献：
  名称：

  Solid-Phase Synthesis of Piperidines by N-Acyliminium Ion Chemistry

  摘要：

  An efficient solid-phase procedure for the synthesis of a number of 2-substituted piperidines is reported. Starting from solid-supported carbamate-tethered delta-amino acetals, 2-benzotriazolyl-substituted (Bt-substituted) piperidines were obtained by acid-induced ring-closure followed by trapping of the transient N-acyliminium ions with benzotriazole. These 2-Bt-substituted piperidines were then used as precursors for the successful introduction of several C-nucleophiles by N-acyliminium. ion chemistry. (C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

  DOI：

  10.1002/1099-0690(200209)2002:18<3133::aid-ejoc3133>3.0.co;2-h

文献信息

• The stereochemistry of the addition of titanium enolates of N-propionyl-oxazolidin-2-ones to 5- and 6-membered N-acyliminium ions
  作者：Ronaldo A. Pilli、Conceição de Fátima Alves、Maria Alice Böckelmann、Yvonne P. Mascarenhas、J. Geraldo Nery、Ivo Vencato

  DOI：10.1016/s0040-4039(99)00398-6

  日期：1999.4

  The stereochemistry of the addition of the N-propionyl titanium enolates 2a and 2b to 5- and 6-membered 2-ethoxycarbamates 1a-f was investigated. The addition proceeded stereoselectively to afford the corresponding (2S,1′S)-2-substituted pyrrolidines as the major diastereoisomer. Despite the lack of reactivity between 2-ethoxypiperidines 1b and N-propionyl titanium enolates 2a and 2b, less bulky carbamate

  研究了向5-和6-元2-乙氧基氨基甲酸酯1a-f添加N-丙酰基钛烯醇酸酯2a和2b的立体化学。添加进行立体选择，得到相应的（2S，1'S）-2-取代的吡咯烷作为主要的非对映异构体。尽管2-乙氧基哌啶1b和N-丙酰基钛烯醇酸酯2a和2b之间缺乏反应性，但2-乙氧基哌啶1d和1f上的氨基甲酸酯基团较少 尽管非对映体选择性较差，但仍能以中等至良好的收率获得恢复的反应性和相应的2-取代的哌啶。
• Reduction of N-Alkoxycarbonyllactams with NaBH4/EtOh-H+: A Facile Synthesis of a-Ethoxyurethanes
  作者：Tatsuo Nagasaka、Hirohisa Tamano、Fumiko Hamaguchi

  DOI：10.3987/r-1986-05-1231

  日期：——
• NAGASAKA TATSUO; TAMANO HIROHISA; HAMAGUCHI FUMIKO, HETEROCYCLES, 24,(1986) N 5, 1231-1232
  作者：NAGASAKA TATSUO、 TAMANO HIROHISA、 HAMAGUCHI FUMIKO

  DOI：——

  日期：——
• US4234484A
  申请人：——

  公开号：US4234484A

  公开（公告）日：1980-11-18
• Short Synthesis of Methylphenidate and Its<i>p</i>-Methoxy Derivative
  作者：Luiz C. Dias、Anna Maria、A. de Piloto Fernandes

  DOI：10.1080/00397910008087153

  日期：2000.4

  A short method for the preparation of racemic threo- and erythro-methylphenidate derivatives is described. Condensation between a-ethoxy carbamate 1 and silyl ketene acetals 2a-b in the presence of TESOTf (20 mol%) afforded a 1.5:1 mixture of carbamates 3a-b/4a-b. Hydrogenolysis in EtOH followed by treatment with 3N HCl/MeOH afforded the corresponding hydrochlorides 7a-b/8a-b in good yields.