nalbuphone hydrochloride | 16676-34-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: nalbuphone hydrochloride
• 英文别名: 6-ketonalbuphine hydrochloride
• CAS: 16676-34-9
• 化学式: C₂₁H₂₅NO₄*ClH
• 分子量: 391.895
• InChiKey: GXRHBZLGLMFDHB-OPHZJPRHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.34
• 重原子数：
  27.0
• 可旋转键数：
  2.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  70.0
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  nalbuphone hydrochloride 在 sodium hydroxide 、 二氧化硫脲 、 盐酸 作用下， 以 水 为溶剂， 反应 1.0h， 以55.1%的产率得到(5alpha,6beta)-17-(环丁基甲基)-4,5-环氧-吗喃-3,6,14-三醇盐酸盐
  参考文献：
  名称：

  One-Pot Process for Synthesis of Nalbuphine Hydrochloride and Impurity Control Strategy

  摘要：

  An improved kilogram-scale process of synthesis of nalbuphine was developed by investigating the critical parameters. Ten process-related impurities were identified, of which the source and control strategy was elucidated. Moreover, tetramethylammonium triacetoxyborohydride (Me4NBH(OAc)(3)) was developed to reduce the imine and ketone in one pot. As a result, 6-beta-epimer was significantly controlled to only 0.08% in the crude nalbuphine. The improved process was robust at kilogram scale in 60.4% overall yield with 99.95% high-performance liquid chromatography (HPLC) purity.

  DOI：

  10.1021/acs.oprd.0c00321
• 作为产物：
  描述：

  14-羟基二氢降吗啡酮盐酸盐 在 盐酸 作用下， 以 四氢呋喃 、 水 、 二甲基亚砜 为溶剂， 反应 1.67h， 生成 nalbuphone hydrochloride
  参考文献：
  名称：

  One-Pot Process for Synthesis of Nalbuphine Hydrochloride and Impurity Control Strategy

  摘要：

  An improved kilogram-scale process of synthesis of nalbuphine was developed by investigating the critical parameters. Ten process-related impurities were identified, of which the source and control strategy was elucidated. Moreover, tetramethylammonium triacetoxyborohydride (Me4NBH(OAc)(3)) was developed to reduce the imine and ketone in one pot. As a result, 6-beta-epimer was significantly controlled to only 0.08% in the crude nalbuphine. The improved process was robust at kilogram scale in 60.4% overall yield with 99.95% high-performance liquid chromatography (HPLC) purity.

  DOI：

  10.1021/acs.oprd.0c00321

文献信息

• PROCESS FOR MAKING MORPHINAN-6alpha-OLS
  申请人：Rezaie Robert

  公开号：US20100036128A1

  公开（公告）日：2010-02-11

  The present invention provides a process whereby morphinan-6-ones can be converted stereospecifically to the corresponding morphinan-6α-ols by catalytic hydrogenation under basic conditions.

  本发明提供了一种方法，通过在碱性条件下催化加氢，可以将吗啡啉-6-酮立体特异地转化为相应的吗啡啉-6α-醇。