sodium 5-methyl-3-nitromethyl-hexanoate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: sodium 5-methyl-3-nitromethyl-hexanoate
• 英文别名: (s)-5-Methyl-3-nitromethyl-hexanoic acid sodium salt；sodium;(3S)-5-methyl-3-(nitromethyl)hexanoate
• 化学式: C₈H₁₄NO₄*Na
• 分子量: 211.193
• InChiKey: CJNCICPERJOSOR-FJXQXJEOSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -2.93
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  86
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  sodium 5-methyl-3-nitromethyl-hexanoate 在 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 6.0h， 以95%的产率得到普瑞巴林
  参考文献：
  名称：

  Development and Scale-up of an Organocatalytic Enantioselective Process to Manufacture (S)-Pregabalin

  摘要：

  Herein is reported the development of a new process to manufacture (S)-pregabalin. The method comprises six steps, run under the catalysis of a recyclable polymer bound phase transfer catalyst, and afforded (S)-pregabalin in overall 54% yield, starting from building blocks acetylacetone, isovaleraldehyde, and nitromethane.

  DOI：

  10.1021/acs.oprd.5b00160
• 作为产物：
  描述：

  普瑞巴林杂质76 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以45.6%的产率得到sodium 5-methyl-3-nitromethyl-hexanoate
  参考文献：
  名称：

  [EN] METHOD FOR THE PREPARATION OF BETA-SUBSTITUTED GAMMA-AMINO CARBOXYLIC ACIDS
  [FR] PROCÉDÉ POUR LA PRÉPARATION D'ACIDES GAMMA-AMINOCARBOXYLIQUES SUBSTITUÉS EN POSITION BÊTA

  摘要：

  本发明涉及通过一锅法将β-取代γ-硝基二羧酸酯或一般式的β-取代γ-硝基二羧酸酯转化为β-取代γ-硝基羧酸，然后将γ-硝基还原为胺基，从而制备β-取代γ-氨基羧酸，优选为对映富集或甚至对映纯形式。特别是，本发明涉及(S)-盐酸普拉巴林的制备。此外，还描述了对映富集的β-取代γ-氨基羧酸和β-取代γ-硝酸盐的形成。

  公开号：

  WO2015189068A1

文献信息

• [EN] PREPARATION OF ENANTIOMERICALLY ENRICHED GAMMA-NITRO ACID AND PREGABALIN<br/>[FR] PROCÉDÉ DE PRÉPARATION D'ACIDE GAMMA-NITRO ENRICHI EN ÉNANTIOMÈRE ET DE PRÉGABALINE
  申请人：MATRIX LAB LTD

  公开号：WO2010004577A1

  公开（公告）日：2010-01-14

  The present invention provides a novel process for the preparation of enantiomerically enriched γ-nitro acid used an intermediate for the preparation of Pregabalin and further conversion to Pregabalin.

  本发明提供了一种制备对映富集的γ-硝基酸的新工艺，用作Pregabalin制备的中间体，并进一步转化为Pregabalin的过程。
• PROCESS FOR THE STEREOSELECTIVE ENZYMATIC HYDROLYSIS OF 5-METHYL-3-NITROMETHYL-HEXANOIC ACID ESTER
  申请人：Albert Martin

  公开号：US20110165636A1

  公开（公告）日：2011-07-07

  The present invention relates to processes for the preparation of 5-methyl-3-nitromethyl-hexanoic acid ester and its salts. Also disclosed are processes for the preparation of 5-methyl-3-nitromethyl-hexanoic acid salt and a process for the preparation of 3-(aminomethyl)-5-methylhexanoic acid. (S)-5-Methyl-3-nitromethyl-hexanoic acid or (R)-5-methyl-3-nitromethyl-hexanoic acid in enantioenriched form or enantiopure form as well as salts thereof, (S)-5-methyl-3-nitromethyl-hexanoic acid ester or (R)-5-methyl-3-nitromethyl-hexanoic acid ester in enantioenriched form or enantiopure form and a compound, namely Formula (XIII), in racemic form, enantioenriched form or enantiopure form are also disclosed.

  本发明涉及制备5-甲基-3-硝基甲基己酸酯及其盐的过程。还公开了制备5-甲基-3-硝基甲基己酸盐的过程和制备3-(氨甲基)-5-甲基己酸的过程。本发明还公开了(S)-5-甲基-3-硝基甲基己酸或(R)-5-甲基-3-硝基甲基己酸的对映富集形式或对映纯形式及其盐，(S)-5-甲基-3-硝基甲基己酸酯或(R)-5-甲基-3-硝基甲基己酸酯的对映富集形式或对映纯形式，以及一种化合物，即公式(XIII)，其为外消旋体、对映富集形式或对映纯形式。
• Process for the stereoselective enzymatic hydrolysis of 5-methyl-3-nitromethyl-hexanoic acid ester
  申请人：Albert Martin

  公开号：US08546112B2

  公开（公告）日：2013-10-01

  The present invention relates to processes for the preparation of 5-methyl-3-nitromethyl-hexanoic acid ester and its salts. Also disclosed are processes for the preparation of 5-methyl-3-nitromethyl-hexanoic acid salt and a process for the preparation of 3-(aminomethyl)-5-methylhexanoic acid. (S)-5-Methyl-3-nitromethyl-hexanoic acid or (R)-5-methyl-3-nitromethyl-hexanoic acid in enantioenriched form or enantiopure form as well as salts thereof, (S)-5-methyl-3-nitromethyl-hexanoic acid ester or (R)-5-methyl-3-nitromethyl-hexanoic acid ester in enantioenriched form or enantiopure form and a compound, namely Formula (XIII), in racemic form, enantioenriched form or enantiopure form are also disclosed.

  本发明涉及制备5-甲基-3-硝基甲基己酸酯及其盐的过程。还揭示了制备5-甲基-3-硝基甲基己酸盐和3-(氨甲基)-5-甲基己酸的过程。本发明还揭示了(S)-5-甲基-3-硝基甲基己酸或(R)-5-甲基-3-硝基甲基己酸的对映富集形式或对映纯形式及其盐，(S)-5-甲基-3-硝基甲基己酸酯或(R)-5-甲基-3-硝基甲基己酸酯的对映富集形式或对映纯形式，以及一种化合物，即公式(XIII)，其为外消旋体、对映富集形式或对映纯形式。
• US8546112B2
  申请人：——

  公开号：US8546112B2

  公开（公告）日：2013-10-01
• [EN] PROCESS FOR THE STEREOSELECTIVE ENZYMATIC HYDROLYSIS OF 5-METHYL-3-NITROMETHYL-HEXANOIC ACID ESTER<br/>[FR] PROCÉDÉ POUR L'HYDROLYSE ENZYMATIQUE STÉRÉOSÉLECTIVE D'UN ESTER D'ACIDE 5-MÉTHYL-3-NITROMÉTHYL-HEXANOÏQUE
  申请人：SANDOZ AG

  公开号：WO2009141362A2

  公开（公告）日：2009-11-26

  The present invention relates to processes for the preparation of 5-methyl-3-nitromethyl-hexanoic acid ester and its salts. Also disclosed are processes for the preparation of 5-methyl-3-nitromethyl-hexanoic acid salt and a process for the preparation of 3-(aminomethyl)-5- methylhexanoic acid. (S)-5-Methyl-3-nitromethyl-hexanoic acid or (R)-5-methyl-3-nitromethyl-hexanoic acid in enantioenriched form or enantiopure form as well as salts thereof, (S)-5-methyl-3-nitromethyl-hexanoic acid ester or (R)-5-methyl-3-nitromethyl-hexanoic acid ester in enantioenriched form or enantiopure form and a compound, namely Formula (XIII), in racemic form, enantioenriched form or enantiopure form are also disclosed.