(S)-1-chloro-3-(piperidin-1-yl)propan-2-ol | 1416332-58-5

• 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: (S)-1-chloro-3-(piperidin-1-yl)propan-2-ol
• 英文别名: (2S)-1-chloro-3-piperidin-1-ylpropan-2-ol
• CAS: 1416332-58-5
• 化学式: C₈H₁₆ClNO
• 分子量: 177.674
• InChiKey: IGMZDGBNMCELOE-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-1-chloro-3-(piperidin-1-yl)propan-2-ol 、 乙酸酐 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 以91%的产率得到(S)-1-chloro-3-(piperidin-1-yl)propan-2-yl acetate
  参考文献：
  名称：

  New chemo-enzymatic synthesis of (R)-1-chloro-3-(piperidin-1-yl) propan-2-ol

  摘要：

  The present study deals with the efficient chemo-enzymatic synthesis of enantiopure (R)-1-chloro-3-(piperidin-1-yl) propan-2-ol 3, as an intermediate for (R)-arimoclomol. This intermediate was synthesized from racemic alcohol (RS)-3 using lipases with vinylacetate as the acyl donor in three different ionic liquids (1-butyl-3-methyl imidazolium tetrafluoroborate [BMIM][BF4], 1-butyl-3-methyl imidazolium hexafluorophosphate [BMIM][PF6],and 1-ethyl-3-methyl imidazolium tetrafluoroborate [EMIM][BF4]) in combination with an organic solvent (toluene). Various reaction parameters, such as temperature, time, substrate and enzyme concentration, and reaction medium (organic solvent and ionic liquid) were optimized using Pseudomonas aeruginosa MTCC 5113 lipases (PAL). It was observed that 30 mM of (RS)-3 and 30 mg/mL of PAL in 4 mL of solvent (toluene:[BMIM][BF4]::70:30) using vinyl acetate as the acyl donor at 30 degrees C gave good conversion (C = 50.02%) and enantiomeric excess (ee(P) = 98.91% and ee(S) = 99%) in 18 h. The (S)-1-chloro-3-(piperidin-1-yl) propan-2-yl acetate 4 and (R)-3 were separated by flash chromatography. Compound (R)-3 is a key intermediate for the synthesis of enantiopure arimoclomol and bimoclomol. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.10.008
• 作为产物：
  描述：

  哌啶 在 Pseudomonas aeruginosa MTCC 5113 lipase 、 lithium bromide 作用下， 以 甲苯 为溶剂， 反应 24.08h， 生成 (S)-1-chloro-3-(piperidin-1-yl)propan-2-ol
  参考文献：
  名称：

  New chemo-enzymatic synthesis of (R)-1-chloro-3-(piperidin-1-yl) propan-2-ol

  摘要：

  The present study deals with the efficient chemo-enzymatic synthesis of enantiopure (R)-1-chloro-3-(piperidin-1-yl) propan-2-ol 3, as an intermediate for (R)-arimoclomol. This intermediate was synthesized from racemic alcohol (RS)-3 using lipases with vinylacetate as the acyl donor in three different ionic liquids (1-butyl-3-methyl imidazolium tetrafluoroborate [BMIM][BF4], 1-butyl-3-methyl imidazolium hexafluorophosphate [BMIM][PF6],and 1-ethyl-3-methyl imidazolium tetrafluoroborate [EMIM][BF4]) in combination with an organic solvent (toluene). Various reaction parameters, such as temperature, time, substrate and enzyme concentration, and reaction medium (organic solvent and ionic liquid) were optimized using Pseudomonas aeruginosa MTCC 5113 lipases (PAL). It was observed that 30 mM of (RS)-3 and 30 mg/mL of PAL in 4 mL of solvent (toluene:[BMIM][BF4]::70:30) using vinyl acetate as the acyl donor at 30 degrees C gave good conversion (C = 50.02%) and enantiomeric excess (ee(P) = 98.91% and ee(S) = 99%) in 18 h. The (S)-1-chloro-3-(piperidin-1-yl) propan-2-yl acetate 4 and (R)-3 were separated by flash chromatography. Compound (R)-3 is a key intermediate for the synthesis of enantiopure arimoclomol and bimoclomol. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.10.008

文献信息

• New chemo-enzymatic synthesis of (R)-1-chloro-3-(piperidin-1-yl) propan-2-ol
  作者：Linga Banoth、Thete Karuna Narayan、Brahmam Pujala、Asit K. Chakraborti、Uttam Chand Banerjee

  DOI：10.1016/j.tetasy.2012.10.008

  日期：2012.12

  The present study deals with the efficient chemo-enzymatic synthesis of enantiopure (R)-1-chloro-3-(piperidin-1-yl) propan-2-ol 3, as an intermediate for (R)-arimoclomol. This intermediate was synthesized from racemic alcohol (RS)-3 using lipases with vinylacetate as the acyl donor in three different ionic liquids (1-butyl-3-methyl imidazolium tetrafluoroborate [BMIM][BF4], 1-butyl-3-methyl imidazolium hexafluorophosphate [BMIM][PF6],and 1-ethyl-3-methyl imidazolium tetrafluoroborate [EMIM][BF4]) in combination with an organic solvent (toluene). Various reaction parameters, such as temperature, time, substrate and enzyme concentration, and reaction medium (organic solvent and ionic liquid) were optimized using Pseudomonas aeruginosa MTCC 5113 lipases (PAL). It was observed that 30 mM of (RS)-3 and 30 mg/mL of PAL in 4 mL of solvent (toluene:[BMIM][BF4]::70:30) using vinyl acetate as the acyl donor at 30 degrees C gave good conversion (C = 50.02%) and enantiomeric excess (ee(P) = 98.91% and ee(S) = 99%) in 18 h. The (S)-1-chloro-3-(piperidin-1-yl) propan-2-yl acetate 4 and (R)-3 were separated by flash chromatography. Compound (R)-3 is a key intermediate for the synthesis of enantiopure arimoclomol and bimoclomol. (C) 2012 Elsevier Ltd. All rights reserved.