tert-butyl (3R)-3-(butanoyloxymethyl)piperidine-1-carboxylate | 140695-98-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: tert-butyl (3R)-3-(butanoyloxymethyl)piperidine-1-carboxylate
• CAS: 140695-98-3
• 化学式: C₁₅H₂₇NO₄
• 分子量: 285.384
• InChiKey: WZUVETOACDLIHB-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (3R)-3-(butanoyloxymethyl)piperidine-1-carboxylate 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以91%的产率得到(R)-1-Boc-3-羟甲基哌啶
  参考文献：
  名称：

  酶法制备手性3-（羟甲基）哌啶衍生物

  摘要：

  （R）-3-（羟甲基）-1-哌啶甲酸叔丁酯是通过外消旋醇的对映选择性酯化反应以及相应的丁酸酯的对映选择性水解和随后的化学反应，以脂肪酶P的形式在不超过98％ee的条件下制备的保留的（R）-酯的水解。描述了在公斤规模上可行的后处理程序。

  DOI：

  10.1016/s0957-4166(00)86038-3
• 作为产物：
  描述：

  t-butyl (R,S)-3-<(butyryloxy)methyl>-1-piperidine-carboxylate 生成 tert-butyl (3R)-3-(butanoyloxymethyl)piperidine-1-carboxylate
  参考文献：
  名称：

  酶法制备手性3-（羟甲基）哌啶衍生物

  摘要：

  （R）-3-（羟甲基）-1-哌啶甲酸叔丁酯是通过外消旋醇的对映选择性酯化反应以及相应的丁酸酯的对映选择性水解和随后的化学反应，以脂肪酶P的形式在不超过98％ee的条件下制备的保留的（R）-酯的水解。描述了在公斤规模上可行的后处理程序。

  DOI：

  10.1016/s0957-4166(00)86038-3

文献信息

• Chemical and Enzymatic Resolution of (<i>R,S</i>)-<i>N</i>-(<i>tert</i>-Butoxycarbonyl)-3-hydroxymethylpiperidine
  作者：Animesh Goswami、Jeffrey M. Howell、Edward Y. Hua、K. David Mirfakhrae、Maxime C. Soumeillant、Shankar Swaminathan、Xinhua Qian、Fernando A. Quiroz、Truc C. Vu、Xuebao Wang、Bin Zheng、David R. Kronenthal、Ramesh N. Patel

  DOI：10.1021/op010210b

  日期：2001.7.1

  (S)-N-(tert-Butoxycarbonyl)-3-hydroxymethylpiperidine 1 was made from (R,S)-3-hydroxymethylpiperidine 2 via fractional crystallization of the corresponding L(-)-dibenzoyl tartarate salt 3 followed by hydrolysis and acylation. Lipase from Pseudomonas cepacia was found to be the best enzyme for the stereospecific resolution of (RS)-N-(tert-butoxycarbonyl)-3-hydroxymethylpiperidine 4. (S)-N-(tert-Butoxycarbonyl)-3-hydroxymethylpiperidine I was obtained in 16% yield and >95% enantiomeric excess (ee) by hydrolysis of (R,S)-acetate 5 by lipase PS from Pseudomonas cepacia. Lipase PS-catalyzed esterification of the (RS)-N-(tert-butoxycarbonyl)-3-hydroxymethylpiperidine 4 with succinic anhydride provided the S-hemisuccinate ester 6, which could be easily separated and hydrolyzed by base to the (S)-N-(tert-butoxycarbonyl)-3-hydroxymethylpiperidine 1. The yield and ee could be improved greatly by repetition of the process. Using the repeated esterification procedure(S)-N-(tert-butoxycarbonyl)-3-hydroxymethylpiperidine I was obtained in 32% yield (maximum theoretical yield 50%) and 98.9% ee.
• N-[18F]fluoroethylpiperidin-4-ylmethyl butyrate: a novel radiotracer for quantifying brain butyrylcholinesterase activity by positron emission tomography
  作者：Tatsuya Kikuchi、Ming-Rong Zhang、Nobuo Ikota、Kiyoshi Fukushi、Toshimitsu Okamura、Kazutoshi Suzuki、Yasushi Arano、Toshiaki Irie

  DOI：10.1016/j.bmcl.2004.01.080

  日期：2004.4

  In Alzheimer's disease, cerebral cortical butyrylcholinesterase (BChE) activity is reported to be elevated. Our aim was to develop a novel F-18-labeled tracer for quantifying cerebral BChE activity by positron emission tomography. With in vitro screening of N-[C-14]ethylpiperidin-3- and 4-ylmethyl esters, N-[C-14]ethylpiperidin-4-ylmethyl butyrate was selected as a lead for F-18-labeling, affording N-[F-18]fluoroethylpiperidin-4-ylmethyl butyrate. The F-18-labeled butyrate showed the required properties for in vivo BChE measurement, that is, the lipophilic nature of the authentic ester, high specificity to B3ChE, a moderate hydrolysis rate, and the hydrophilic nature of the metabolite. (C) 2004 Elsevier Ltd. All rights reserved.
• Enzymatic preparation of chiral 3-(hydroxymethyl)piperidine derivatives
  作者：Beat Wirz、Willy Walther

  DOI：10.1016/s0957-4166(00)86038-3

  日期：1992.8

  t-Butyl (R)-3-(hydroxymethyl)-1-piperidinecarboxylate was prepared with lipase P in up to 98 % ee by means of enantioselective esterification of the racemic alcohol as well as by enantioselective hydrolysis of the corresponding butyryl ester and subsequent chemical hydrolysis of the retained (R)-ester. A work-up procedure feasible on the kg-scale is described.

  （R）-3-（羟甲基）-1-哌啶甲酸叔丁酯是通过外消旋醇的对映选择性酯化反应以及相应的丁酸酯的对映选择性水解和随后的化学反应，以脂肪酶P的形式在不超过98％ee的条件下制备的保留的（R）-酯的水解。描述了在公斤规模上可行的后处理程序。