[11C]-R 116301

• 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: [11C]-R 116301
• 英文别名: [3H]-R 116301；R 116301；(+)-(B-trans)-4-[1-[3,5-bis(trifluoromethyl)benzoyl]-2-(phenylmethyl)-4-piperidinyl]-N-(2,6-dimethylphenyl)-1-piperazineacetamide*(L)-malic acid；2-[4-[(2R,4S)-2-benzyl-1-[3,5-bis(trifluoromethyl)benzoyl]piperidin-4-yl]piperazin-1-yl]-N-(2,6-dimethylphenyl)acetamide;(2S)-2-hydroxybutanedioic acid
• 化学式: C₄H₆O₅*C₃₅H₃₈F₆N₄O₂
• 分子量: 794.791
• InChiKey: AVMOAPUQICCOKV-WLCUPQJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.72
• 重原子数：
  56
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  151
• 氢给体数：
  4
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  4,4-(乙烯二氧基)-1-叔丁氧羰基哌啶 在 titanium(IV) isopropylate 、 四甲基乙二胺 、 5%-palladium/activated carbon 、 potassium tert-butylate 、 氢气 、 仲丁基锂 、 sodium carbonate 、 三乙胺 、 sodium hydroxide 作用下， 以 甲醇 、 乙醚 、 异丙醇 为溶剂， -70.0~100.0 ℃ 、100.0 kPa 条件下， 反应 49.33h， 生成 [11C]-R 116301
  参考文献：
  名称：

  Process Development of the Synthetic Route to R116301

  摘要：

  We describe in this paper the synthesis of compound 1 (R116301), which was developed to prepare pilot scale quantities (20-50 kg) of drug substance. The synthesis involves the (BuLi)-Bu-s deprotonation of Boc-protected piperidone acetal 2, followed by benzaldehyde addition and ring closure to cyclic carbamate 4. Piperidine acetal 5 is resolved with Brown's acid and acylated. The ketone obtained after piperidine acetal deprotection undergoes reductive amination with N-benzyl piperazine, the most critical step in the synthesis. After debenzylation, final coupling and salt formation, compound 1 is obtained over 10 steps with 4% overall yield.

  DOI：

  10.1021/op700086d

文献信息

• Process Development of the Synthetic Route to R116301
  作者：Michel Guillaume、Jef Cuypers、Jul Dingenen

  DOI：10.1021/op700086d

  日期：2007.11.1

  We describe in this paper the synthesis of compound 1 (R116301), which was developed to prepare pilot scale quantities (20-50 kg) of drug substance. The synthesis involves the (BuLi)-Bu-s deprotonation of Boc-protected piperidone acetal 2, followed by benzaldehyde addition and ring closure to cyclic carbamate 4. Piperidine acetal 5 is resolved with Brown's acid and acylated. The ketone obtained after piperidine acetal deprotection undergoes reductive amination with N-benzyl piperazine, the most critical step in the synthesis. After debenzylation, final coupling and salt formation, compound 1 is obtained over 10 steps with 4% overall yield.