(R)-1-cyclopropyl-2-methoxyethanamine | 1141017-22-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-1-cyclopropyl-2-methoxyethanamine
• 英文别名: (1R)-1-cyclopropyl-2-methoxyethanamine
• CAS: 1141017-22-2
• 化学式: C₆H₁₃NO
• 分子量: 115.175
• InChiKey: APFVIOCNPBAUSZ-LURJTMIESA-N

物化性质

• 沸点：
  161.6±13.0 °C(Predicted)
• 密度：
  0.998±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-1-cyclopropyl-2-methoxyethanamine 在 甲醇 、 sodium tetrahydroborate 、 sodium sulfate 、 HATU 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 (R)-tert-butyl (3-cyclopropyl-5-(2-((1-cyclopropyl-2-methoxyethyl)((5-(trifluoromethyl)pyridin-2-yl)methyl)amino)-2-oxoacetamido)pyridin-2-yl)carbamate
  参考文献：
  名称：

  [EN] COMPOUNDS AND METHODS OF USE
  [FR] COMPOSÉS ET PROCÉDÉS D'UTILISATION

  摘要：

  提供了式(A)化合物：式（A）；及其药学上可接受的盐，以及其药物组合物、制备工艺和处理方法；其中 Ra、Ra'、环 A、环 B 和 R1 如本文所述的任一实施方案中所定义。

  公开号：

  WO2023146987A1
• 作为产物：
  描述：

  1-环丙基-2-甲氧基乙胺 、 sodium pyruvate 在 Vibrio fluvalis (Julich) ω-transaminase 作用下， 反应 160.0h， 生成 (R)-1-cyclopropyl-2-methoxyethanamine 、 (S)-1-cyclopropyl-2-methoxyethanamine 、 、
  参考文献：
  名称：

  Preparation of (S)-1-Cyclopropyl-2-methoxyethanamine by a Chemoenzymatic Route Using Leucine Dehydrogenase

  摘要：

  (S)-1-Cyclopropyl-2-methoxyethanamine is a key chiral intermediate for the synthesis of a corticotropin-releasing factor-1(CRF-1) receptor antagonist. Resolution of the racemic amine by transaminase from Vibrio fluvalis gave a 38% yield of the S-amine with 53% ee. Resolution by lipase-catalyzed acylation provided the S-amine in 35% yield with 91% ee. With limited success of these resolution approaches, an efficient chemo-enzymatic route to (S)-1-cyclopropyl-2-methoxyethanamine was devised starting from methylcyclopropyl ketone. Permanganate oxidation of the ketone gave cyclopropylglyoxylic acid, which was converted to (S)-cyclopropylglycine by reductive amination using leucine dehydrogenase from Thermoactinomyces intermedius with NADH cofactor recycling by formate dehydrogenase from Pichia pastoris. Both enzymes were cloned and expressed in recombinant E. coli. (S)-Cyclopropylglycine obtained from enzymatic reductive amination was isolated as the N-Boc derivative and converted to the desired amine by reduction, methylation, and deprotection to give (S)1-cyclopropyl-2-methoxyethanamine in 62% overall yield from cyclopropylglyoxylic acid, with no detectable R-enantiomer.

  DOI：

  10.1021/op2003562

文献信息

• Preparation of (<i>S</i>)-1-Cyclopropyl-2-methoxyethanamine by a Chemoenzymatic Route Using Leucine Dehydrogenase
  作者：William L. Parker、Ronald L. Hanson、Steven L. Goldberg、Thomas P. Tully、Animesh Goswami

  DOI：10.1021/op2003562

  日期：2012.3.16

  (S)-1-Cyclopropyl-2-methoxyethanamine is a key chiral intermediate for the synthesis of a corticotropin-releasing factor-1(CRF-1) receptor antagonist. Resolution of the racemic amine by transaminase from Vibrio fluvalis gave a 38% yield of the S-amine with 53% ee. Resolution by lipase-catalyzed acylation provided the S-amine in 35% yield with 91% ee. With limited success of these resolution approaches, an efficient chemo-enzymatic route to (S)-1-cyclopropyl-2-methoxyethanamine was devised starting from methylcyclopropyl ketone. Permanganate oxidation of the ketone gave cyclopropylglyoxylic acid, which was converted to (S)-cyclopropylglycine by reductive amination using leucine dehydrogenase from Thermoactinomyces intermedius with NADH cofactor recycling by formate dehydrogenase from Pichia pastoris. Both enzymes were cloned and expressed in recombinant E. coli. (S)-Cyclopropylglycine obtained from enzymatic reductive amination was isolated as the N-Boc derivative and converted to the desired amine by reduction, methylation, and deprotection to give (S)1-cyclopropyl-2-methoxyethanamine in 62% overall yield from cyclopropylglyoxylic acid, with no detectable R-enantiomer.
• [EN] COMPOUNDS AND METHODS OF USE<br/>[FR] COMPOSÉS ET PROCÉDÉS D'UTILISATION
  申请人：TANGO THERAPEUTICS INC

  公开号：WO2023146987A1

  公开（公告）日：2023-08-03

  Provided are compounds of Formula (A): Formula (A); and pharmaceutically acceptable salts thereof, and pharmaceutical compositions, processes of preparing and methods of treating thereof; wherein Ra, Ra', Ring A, Ring B, and R1are as defined in any of the embodiments described herein.

  提供了式(A)化合物：式（A）；及其药学上可接受的盐，以及其药物组合物、制备工艺和处理方法；其中 Ra、Ra'、环 A、环 B 和 R1 如本文所述的任一实施方案中所定义。