tert-butyl (3S)-3-[(1S)-1-[(6-chloro-2-methyl-3-pyridyl)oxy]-3-methyl-butyl]pyrrolidine-1-carboxylate | 1433439-80-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: tert-butyl (3S)-3-[(1S)-1-[(6-chloro-2-methyl-3-pyridyl)oxy]-3-methyl-butyl]pyrrolidine-1-carboxylate
• CAS: 1433439-80-5
• 化学式: C₂₀H₃₁ClN₂O₃
• 分子量: 382.931
• InChiKey: WRBOMTYITJQYAB-RDJZCZTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.09
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  51.66
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (3S)-3-[(1S)-1-[(6-chloro-2-methyl-3-pyridyl)oxy]-3-methyl-butyl]pyrrolidine-1-carboxylate 在 sodium methylate 、 苯甲醚 、 三氟乙酸 作用下， 以 四氢呋喃 、 二甲基亚砜 、 乙腈 为溶剂， 反应 1.08h， 生成 6-methoxy-2-methyl-3-[(1S)-3-methyl-1-[(3S)-pyrrolidin-3-yl]butoxy]pyridine D-tartrate
  参考文献：
  名称：

  Discovery of a Potent, Dual Serotonin and Norepinephrine Reuptake Inhibitor

  摘要：

  The objective of the described research effort was to identify novel serotonin and norepinephrine reuptake inhibitor (SNRI) with improved norepinephrine transporter activity and acceptable metabolic stability and exhibiting minimal drug-drug interaction. We describe herein the discovery of a series of 3-substituted pyrrolidines exemplified by compound 1. Compound 1 is a selective SNRI in vitro and in vivo has favorable ADME properties, and retains inhibitory activity in the formalin model of pain behavior. Compound 1 thus represents a potential new probe to explore utility of SNRIs in central nervous system disorders, including,chronic: pain conditions.

  DOI：

  10.1021/ml400049p
• 作为产物：
  描述：

  2-氯-5-氟-6-甲基吡啶 、 度洛西汀 在 sodium hydride 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 27.0h， 以87%的产率得到tert-butyl (3S)-3-[(1S)-1-[(6-chloro-2-methyl-3-pyridyl)oxy]-3-methyl-butyl]pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Discovery of a Potent, Dual Serotonin and Norepinephrine Reuptake Inhibitor

  摘要：

  The objective of the described research effort was to identify novel serotonin and norepinephrine reuptake inhibitor (SNRI) with improved norepinephrine transporter activity and acceptable metabolic stability and exhibiting minimal drug-drug interaction. We describe herein the discovery of a series of 3-substituted pyrrolidines exemplified by compound 1. Compound 1 is a selective SNRI in vitro and in vivo has favorable ADME properties, and retains inhibitory activity in the formalin model of pain behavior. Compound 1 thus represents a potential new probe to explore utility of SNRIs in central nervous system disorders, including,chronic: pain conditions.

  DOI：

  10.1021/ml400049p