N-tert-butoxycarbonyl-(2R,3R)-3-methyl-3-hydroxypiperidine-2-carboxylic acid | 1019848-24-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-tert-butoxycarbonyl-(2R,3R)-3-methyl-3-hydroxypiperidine-2-carboxylic acid
• 英文别名: (2R,3R)-3-hydroxy-3-methyl-1-[(2-methylpropan-2-yl)oxycarbonyl]piperidine-2-carboxylic acid
• CAS: 1019848-24-8
• 化学式: C₁₂H₂₁NO₅
• 分子量: 259.302
• InChiKey: GWKYNESZIVLJCG-QPUJVOFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  87.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-tert-butoxycarbonyl-(2S,3R)-3-methyl-3-hydroxypiperidine-2-methanol 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 sodium chlorite 作用下， 以 phosphate buffer 、 乙腈 为溶剂， 反应 6.0h， 以84%的产率得到N-tert-butoxycarbonyl-(2R,3R)-3-methyl-3-hydroxypiperidine-2-carboxylic acid
  参考文献：
  名称：

  A Short Enantioselective Synthesis of N-Boc-(2R,3R)-3-Methyl-3-Hydroxypipecolic Acid from Geraniol

  摘要：

  The asymmetric synthesis of (2R,3R)-3-methyl-3-hydroxypipecolic acid, a key intermediate in the synthesis of dual MMP-13/aggrecanase inhibitors, is described. The title compound is prepared in seven steps with an overall yield of 41% starting from geraniol. Key steps in the synthesis include Sharpless asymmetric epoxidation, which establishes the chiral centers, and a one-pot oxidative olefin cleavage/reductive amination sequence that closes the piperidine ring.

  DOI：

  10.1021/jo800080t

文献信息

• [EN] AN ENANTIOSELECTIVE PROCESS FOR THE SYNTHESIS OF (2S,4R)-4-HYDROXYPIPECOLIC ACID<br/>[FR] PROCÉDÉ ÉNANTIOSÉLECTIF DE SYNTHÈSE D'ACIDE (2S,4R)-4-HYDROXYPIPÉCOLIQUE
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2016120890A1

  公开（公告）日：2016-08-04

  The present invention relates to an improved process for synthesis of 4-hydroxy pipecolic acid. The present invention relates to an improved enantioselective process for the synthesis of (2S,4R)-4-hydroxypipecolic acid via Co(III) (salen)-catalyzed two stereocentered Hydrolytic Kinetic Resolution (HKR) of racemic 1,3-azido epoxide with good yields and high optical purity without any protecting groups. 10 31

  本发明涉及一种改进的合成4-羟基吡哆酸的方法。本发明涉及一种改进的不对称选择性过程，用于通过Co(III) (salen)催化的两个立体中心水解动力学分辨（HKR）合成(2S,4R)-4-羟基吡哆酸，具有良好的产率和高光学纯度，且无需任何保护基团。
• A Short Enantioselective Synthesis of <i>N</i>-Boc-(2<i>R</i>,3<i>R</i>)-3-Methyl-3-Hydroxypipecolic Acid from Geraniol
  作者：Mark C. Noe、Joel M. Hawkins、Sheri L. Snow、Lilli Wolf-Gouveia

  DOI：10.1021/jo800080t

  日期：2008.4.1

  The asymmetric synthesis of (2R,3R)-3-methyl-3-hydroxypipecolic acid, a key intermediate in the synthesis of dual MMP-13/aggrecanase inhibitors, is described. The title compound is prepared in seven steps with an overall yield of 41% starting from geraniol. Key steps in the synthesis include Sharpless asymmetric epoxidation, which establishes the chiral centers, and a one-pot oxidative olefin cleavage/reductive amination sequence that closes the piperidine ring.