BOC-pseudoephedrine | 152614-95-4

• 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: BOC-pseudoephedrine
• 英文别名: (1S,2S)-1-Phenyl-2-(methyl tert-butoxycarbonylamino)-1-propanol；tert-butyl N-[(1S,2S)-1-hydroxy-1-phenylpropan-2-yl]-N-methylcarbamate
• CAS: 152614-95-4
• 化学式: C₁₅H₂₃NO₃
• 分子量: 265.353
• InChiKey: SIKODEFLCMOILM-WCQYABFASA-N

物化性质

• 沸点：
  377.3±31.0 °C(Predicted)
• 密度：
  1.073±0.06 g/cm3(Predicted)
• 溶解度：
  DMF：30mg/mL； DMSO：30mg/mL；乙醇：20mg/mL； PBS（pH 7.2）：10 mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  BOC-pseudoephedrine 在 盐酸 、 potassium carbonate 作用下， 以 水 、 乙酸乙酯 、 异丙醇 为溶剂， 反应 40.5h， 生成 盐酸苄非他明
  参考文献：
  名称：

  An Efficient, Scalable Process for Benzphetamine Hydrochloride

  摘要：

  Commercial manufacturing of benzphetamine hydrochloride along with its impurity profiling is disclosed. Deoxygenation of pseudoephedrine is reported with similar to 100% retention by shielding the amine group as its tert-butyl carbamate, which is very straightforward to eliminate at the end. Four unknown process-related impurities are isolated from the samples of final API and characterized on the basis of their NMR and mass spectral analysis. Structures of the isolated impurities are confirmed by independent syntheses and coinjecting with the isolated one.

  DOI：

  10.1021/op400313y
• 作为产物：
  描述：

  麻黄碱盐酸盐 生成 BOC-pseudoephedrine
  参考文献：
  名称：

  Org. Process Res. Dev. 2014, 18, 495-500

  摘要：

  DOI：

文献信息

• Chiral oxazolidinones from N-Boc derivatives of β-amino alcohols. Effect of a N-methyl substituent on reactivity and stereoselectivity
  作者：Claude Agami、François Couty、Louis Hamon、Olivier Venier

  DOI：10.1016/0040-4039(93)88071-p

  日期：1993.7

  Treatment of N-tert-butoxycarbonyl derivatives of homochiral β-amino alcohols with p-toluenesulfonyl chloride affords 2-axazolidinones. These heterocycles were produced by intramolecular nucleophilic attack of the carbamate moiety in an intermediate tosylate. The presence of a N-methyl substituent enhanced the cyclization rate and this effect was studied by AM1 calculations.

  用对甲苯磺酰氯处理高手性β-氨基醇的N-叔丁氧基羰基衍生物，得到2-ax唑烷酮。这些杂环是通过中间体甲苯磺酸酯中氨基甲酸酯部分的分子内亲核攻击产生的。N-甲基取代基的存在增强了环化速率，并且通过AM1计算研究了该效应。
• Diastereoselective reduction of α-aminoketones: Synthesis of <i>anti</i>- and <i>syn</i>-β-aminoalcohols
  作者：David S Fraser、Sheldon B Park、J Michael Chong

  DOI：10.1139/v03-165

  日期：2004.2.1

  Reduction of N-t-BOC-protected-N-alkyl α-aminoketones with LiEt₃BH or Li(s-Bu)₃BH furnishes protected syn-β-aminoalcohols with high selectivities. In contrast, removal of the BOC group followed by reduction of the aminoketone gives anti-β-aminoalcohols with variable selectivities. With aromatic ketones, selectivities are typically high while aliphatic ketones show mediocre to high selectivities depending on steric considerations.Key words: β-aminoalcohol, diastereoselective reduction.

  N-t-BOC保护的N-烷基α-氨基酮通过LiEt3BH或Li(s-Bu)3BH还原得到具有高选择性的保护的同型β-氨基醇。相反，去除BOC基团后再还原氨基酮会得到具有可变选择性的反型β-氨基醇。对于芳香酮，选择性通常很高，而脂肪族酮则根据立体位阻考虑显示出一般到高的选择性。关键词：β-氨基醇，对映选择性还原。
• Application of the Mitsunobu reaction to ephedrines and some related amino alcohols. Aspects of intramolecular participation of the amino group
  作者：Martin A. Poelert、Richard M. Kellogg、L. A. Hulshof

  DOI：10.1002/recl.19941130704

  日期：——

  at the benzylic hydroxyl group of (1S,2S)-pseudoephedrine (2) to afford (1R,2S)-ephedrine is known to be a difficult process. The Mitsunobu reactions of 1 and 2 might offer a route to achieve such inversions. In fact Mitsunobu reactions on 1 and 2 are known to proceed via aziridines formed on intramolecular SN2 substitution by the amine functionality. The Mitsunobu reactions of N-methylated and N-benzylated

  已知将（1S，2S）-伪麻黄碱（2）的苄基羟基上的构型反转以得到（1R，2S）-麻黄碱是一个困难的过程。1和2的Mitsunobu反应可能会提供实现此类反演的途径。实际上，已知在1和2上的Mitsunobu反应是通过分子内S N 2被胺官能团取代形成的氮丙啶进行的。已经发现N-甲基化和N-苄基化的麻黄碱的Mitsunobu反应通过相应的叠氮鎓离子进行。这些吖丙啶鎓离子可以被打开（小号N 2取代）被邻苯二甲酰亚胺和硫醇等亲核试剂所取代。通过使用叔丁氧羰基-（BOC）或苄氧羰基-（CBZ）保护的衍生物，可以避免分子内参与2。这些衍生物上的Mitsunobu反应导致苄基羟基中心的构型反转。相反，1的BOC和CBZ衍生物在Mitsunobu条件下脱保护。的光延反应苏式（1小号，2，小号也已经研究了）-2-氨基-1,3-丙二醇。通过与二甲基甲酰胺二甲基乙缩醛反应实现保护的尝试导致了通过X射线晶体学确
• Agami, Claude; Couty, Francois; Hamon, Louis, Bulletin de la Societe Chimique de France, 1995, vol. 132, # 8, p. 808 - 814
  作者：Agami, Claude、Couty, Francois、Hamon, Louis、Venier, Olivier

  DOI：——

  日期：——
• An Efficient, Scalable Process for Benzphetamine Hydrochloride
  作者：Chinmoy Pramanik、Kiran Bapat、Ashok Chaudhari、Mukund G Kulkarni、Rangarao Kolla、Srinivasarao Sompalli、Narendra K. Tripathy、Mukund K. Gurjar

  DOI：10.1021/op400313y

  日期：2014.4.18

  Commercial manufacturing of benzphetamine hydrochloride along with its impurity profiling is disclosed. Deoxygenation of pseudoephedrine is reported with similar to 100% retention by shielding the amine group as its tert-butyl carbamate, which is very straightforward to eliminate at the end. Four unknown process-related impurities are isolated from the samples of final API and characterized on the basis of their NMR and mass spectral analysis. Structures of the isolated impurities are confirmed by independent syntheses and coinjecting with the isolated one.