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盐酸他喷他多的合成 被引量：4

Synthesis of Tapentadol Hydrochloride
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摘要 间甲氧基苯丙酮与二甲胺盐酸盐发生Mannich反应生成消旋3-二甲胺基-1-(3-甲氧基苯基)-2-甲基-1-丙酮(13),经结晶诱导的非对映异构体转化得到S-型化合物14后,经格氏反应、酰化及催化氢解得到(2R,3R)-2-甲基-3-(3-甲氧基苯基)-N,N-二甲基戊胺,最后经脱保护基、与盐酸成盐得到中枢镇痛药盐酸他喷他多,总收率约52%。 The central analgesics tapentadol hydrochloride was synthesized from 1-（3-methoxyphenyl）-1-propanone by Mannich reaction with dimethylamine hydrochloride to obtain racemic 3-dimethylamino-1-（3-methoxyphenyl）-2-methylpropan-1-one（13）,which was subjected to crystallization-induced diastereomer transformation,Grignard reaction,acylation and catalytic hydrogenolysis to give （2R,3R）-2-methyl-3-（3-methoxyphenyl）-N,N-dimethylpentanamine,followed by deprotection and salt formation with an overall yield of about 52%.
作者 马慧 冯文化 梁玉华
机构地区 北京协和医学院药物研究所
出处 《中国医药工业杂志》 CAS CSCD 北大核心 2010年第9期641-644,共4页 Chinese Journal of Pharmaceuticals
关键词 他喷他多 中枢镇痛药 阿片μ受体激动剂 肾上腺素能递质摄取抑制剂 结晶诱导 合成 tapentadol central analgesics opioid μ receptor agonist adrenergic transmitter uptake inhibitor crystallization induction synthesis
分类号 R971.1 [医药卫生—药品]
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参考文献7

  • 1Thompson CA.Tapentadol approved as pain reliever[J].Am J Health Syst Pharm,2009,66(1):8.
  • 2Tzschentke TM,Vry JD,Yerlinden R,et al.Tapentadol hydrochioride analgesic mu-opioid receptor agonist noradrenaline reuptake inhibitor[J].Drug Future,2006,31(12):1053-1061.
  • 3Filliers WFM,Broeckx RLM.Preparation of(2R,3R)-3(3-methoxyphenyl)-N,N,2-trimethylpentanamine:WO,2008012283[P].2008-01-31.(CA2007,148:191726).
  • 4Hell W,Zimmer O,Buschmann HH,et al.Process for the preparation of(1R,2R)-3-(3-dimethylamino-1-ethyl-2methyl-propyl)-phenol:WO,2008012047[P].2008-01-31.(CA 2007,148:191725).
  • 5Hell W.Preparation of 3-[(1R,2R)-3-(dimethylamino)1-ethyl-2-methylpropyl] -phenol:WO,2008012046[P].2008-01-31.(CA2007,148:191724).
  • 6Bushmann H,Strassburger W,Friderichs E.Preparation of 1-phenyl-3-dimethylaminopropane derivatives as analgesics:EP,95110864[P].1995-07-12.(CA 1995,124:288962).
  • 7Hell W,Kegel M,Akteries B,et al.Preparation of substituted 3-arylbutylamines from 1-amino-3-arylbutan-3-ols via elimination and hydrogenation:WO,2004108658[P].2004-12-16.(CA 2004,142:55981).

同被引文献21

  • 1曾雪云,曾敬,陈明,竺来发,刘伟,王胜得.气相色谱法分析2,2-二甲基-4-羟基-1,3-苯并二噁茂[J].精细化工中间体,2019,49(6):67-69. 被引量：4
  • 2Buschmann H, Strassburger W. 1-Phenyl-3-dimethylamino- propane derivatives having pharmacological activity: EP, 95110864 [P]. 1995-07o12. (CA 1995, 124: 288962).
  • 3Hell W, Kegel M, Akteries B, et al. Preparation of substituted 3-arylbutylamines from 1 -amino-3-arylbutan-3-o 1 s via elimination and hydrogenation: WO, 2004108658 [P]. 2004-12-16. (CA2004, 142: 55981).
  • 4Hell W. Preparation of 3-[ (1R,2R)-3-(dimethylamino)- 1-ethyl-2-methylpropyl] phenol: WO, 2008012046 [P]. 2008-01-31. (CA 2007, 148: 191724).
  • 5Hell W, Zimmer O, Buschmann HH, et al. Process for the preparation of 3- [ (1R,2R) -3- (dimethylamino) -l-ethyl-2- methyl-propyl]-phenol: WO, 2008012047 [P]. 2008-01-31. (CA 2007, 148:191725).
  • 6Filliers WFM, Broeckx RLM. Preparation of (2R,3R) -3- (3-methoxypropyl)-N,N,2-trimethylpentanamine: WO, 2008012283 [P]. 2008-01-31. (CA2007, 148: 191726).
  • 7Buschmann H, Strassburger W, Friderichs E. 1-Phenyl-3- dimethylaminopropane compounds with a pharmacological effect: US, 6344558 [P]. 2002-01-24.
  • 8THOMPSON CA. Tapentadol approved as pain reliever[ J]. Am J Health Syst Pharm, 2009, 66 ( 1 ) : 8.
  • 9TZSCHENTKE TM, VRY JD, TERLINDER R, et al. Tapentadol hydrochloride: Analgesic mu-opioid receptor agonist noradrenaline reuptake inhibitor [ J ]. Drug Future, 2006, 31 (12) : 1053 - 1061.
  • 10BUSHMANN H, STRASSBURGER W, FRIDERICHS E. 1-Phen- yl-3-dimethylamino-propane derivatives having pharmacological ac- tivity: EP, 0693475 [ P]. 1996 - 01 - 24.

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中国医药工业杂志
2010年 第9期

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