1-Cbz-cis-3-azido-4-hydroxypyrrolidine

• 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: 1-Cbz-cis-3-azido-4-hydroxypyrrolidine
• 英文别名: benzyl (3S,4R)-3-azido-4-hydroxypyrrolidine-1-carboxylate
• 化学式: C₁₂H₁₄N₄O₃
• 分子量: 262.268
• InChiKey: RIMVJYHSULPFSY-WDEREUQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  64.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-Cbz-cis-3-azido-4-hydroxypyrrolidine 在 Pseudomonas cepacia lipase immobilized on diatomaceous earth 、 sodium hydride 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 正己烷 、 异丙醚 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 39.0h， 生成 1-Cbz-3-[(tert-butoxycarbonyl)methylamino]-4-methoxypyrrolidine
  参考文献：
  名称：

  Chemoenzymatic synthesis of (3R,4S)- and (3S,4R)-3-methoxy-4-methylaminopyrrolidine

  摘要：

  An efficient and a convenient enantio selective synthesis of (3R,4S)-3-methoxy-4-methylaminopyrrolidine has been carried out by a lipase-mediated resolution protocol. This method describes the preparation of (+/-)-l-Cbz-cis-3-azido-4-hydroxypyrrolidine starting from commercially available diallylamine followed by ring-closing metathesis (RCM) via S(N)2 displacement reactions. Pseudomonas cepacia lipase immobilized on diatomaceous earth (Amano PS-D) provides (3R,4S)-11 and (3S,4R)-12 in an excellent enantiomeric excess. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.10.031
• 作为产物：
  描述：

  benzyl diallylcarbamate 在 Grubbs catalyst first generation sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 sodium azide 、 水 、 potassium carbonate 、 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 29.0h， 生成 1-Cbz-cis-3-azido-4-hydroxypyrrolidine
  参考文献：
  名称：

  Chemoenzymatic synthesis of (3R,4S)- and (3S,4R)-3-methoxy-4-methylaminopyrrolidine

  摘要：

  An efficient and a convenient enantio selective synthesis of (3R,4S)-3-methoxy-4-methylaminopyrrolidine has been carried out by a lipase-mediated resolution protocol. This method describes the preparation of (+/-)-l-Cbz-cis-3-azido-4-hydroxypyrrolidine starting from commercially available diallylamine followed by ring-closing metathesis (RCM) via S(N)2 displacement reactions. Pseudomonas cepacia lipase immobilized on diatomaceous earth (Amano PS-D) provides (3R,4S)-11 and (3S,4R)-12 in an excellent enantiomeric excess. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.10.031

文献信息

• Enzymatic resolution of five membered heterocyclic bromohydrins
  作者：Ángela Villar-Barro、Vicente Gotor、Rosario Brieva

  DOI：10.1016/j.tetasy.2013.04.012

  日期：2013.6

  The lipase catalyzed resolution of trans-3,4-tetrahydrofuran and pyrrolidine bromohydrins by acylation or hydrolysis of their acylated derivatives has been studied. For both heterocycles, the best enantioselectivity was obtained using Candida antarctica lipase B as the catalyst in the hydrolytic processes. The enantiomerically pure bromohydrins are useful intermediates for the preparation of 3,4-fuctionalized cis-heterocycles. (C) 2013 Elsevier Ltd. All rights reserved.
• Enzymatic preparation of cis and trans-3-amino-4-hydroxytetrahydrofurans and cis-3-amino-4-hydroxypyrrolidines
  作者：Ángela Villar-Barro、Vicente Gotor、Rosario Brieva

  DOI：10.1016/j.bmc.2014.05.014

  日期：2014.10

  The lipase catalyzed resolution of cis and trans-3-amino-4-hydroxytetrahydraurans and cis-3-amino-4-hydroxypyrrolidines have been studied. For all the heterocycles, the best enantioselectivity was obtained using Candida antarctica lipases A and B as catalysts in hydrolytic processes. The absolute configuration of the optically pure obtained heterocycles has been assigned. (C) 2014 Elsevier Ltd. All rights reserved.
• Chemoenzymatic synthesis of (3R,4S)- and (3S,4R)-3-methoxy-4-methylaminopyrrolidine
  作者：Ahmed Kamal、Ahmad Ali Shaik、Mahendra Sandbhor、M. Shaheer Malik、Shaik Azeeza

  DOI：10.1016/j.tetasy.2006.10.031

  日期：2006.11

  An efficient and a convenient enantio selective synthesis of (3R,4S)-3-methoxy-4-methylaminopyrrolidine has been carried out by a lipase-mediated resolution protocol. This method describes the preparation of (+/-)-l-Cbz-cis-3-azido-4-hydroxypyrrolidine starting from commercially available diallylamine followed by ring-closing metathesis (RCM) via S(N)2 displacement reactions. Pseudomonas cepacia lipase immobilized on diatomaceous earth (Amano PS-D) provides (3R,4S)-11 and (3S,4R)-12 in an excellent enantiomeric excess. (c) 2006 Elsevier Ltd. All rights reserved.