(2S,4R)-1-Boc-2-氰基-4-羟基吡咯烷 | 483366-12-7

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: (2S,4R)-1-Boc-2-氰基-4-羟基吡咯烷
• 英文名称: (2S,4R)-N-Boc-2-cyano-4-hydroxypyrrolidine
• 英文别名: (2S,4R)-1-(tert-butoxycarbonyl)-4-hydroxypyrolidine-2-carbonitrile；tert-butyl (2S,4R)-2-cyano-4-hydroxy-pyrrolidine-1-carboxylate；(2S,4R)-tert-butyl 2-cyano-4-hydroxypyrrolidine-1-carboxylate；(2S,4R)-1-Boc-2-cyano-4-hydroxypyrrolidine；tert-butyl (2S,4R)-2-cyano-4-hydroxypyrrolidine-1-carboxylate
• CAS: 483366-12-7
• 化学式: C₁₀H₁₆N₂O₃
• 分子量: 212.249
• InChiKey: UNVNZVOSYRUJTH-JGVFFNPUSA-N

物化性质

• 沸点：
  361.4±42.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  73.6
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: (2S,4R)-1-Boc-2-cyano-4-hydroxypyrrolidine
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: (2S,4R)-1-Boc-2-cyano-4-hydroxypyrrolidine
CAS number: 483366-12-7

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C10H16N2O3
Molecular weight: 212.2

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  (2S,4R)-1-Boc-2-氰基-4-羟基吡咯烷 以100的产率得到1-Boc-(2S,4S)-2-氰-4-氟吡咯烷
  参考文献：
  名称：

  DICYCLOAZAALKANE DERIVATES, PREPARATION PROCESSES AND MEDICAL USES THEREOF

  摘要：

  本发明涉及新的二环氮杂烷衍生物，其通式表示为（I），以及包含它们的制备方法、药物组合物以及用于治疗特别是二肽基肽酶抑制剂（DPP-IV）的用途，其中通式（I）的每个取代基如规范中所定义。

  公开号：

  EP2246347A1
• 作为产物：
  描述：

  (2S,4R)-1-Boc-2-氨基甲酰基-4-羟基吡咯烷 在 吡啶 、 三氟乙酸酐 作用下， 以73%的产率得到(2S,4R)-1-Boc-2-氰基-4-羟基吡咯烷
  参考文献：
  名称：

  DICYCLOAZAALKANE DERIVATES, PREPARATION PROCESSES AND MEDICAL USES THEREOF

  摘要：

  公开号：

  EP2246347B1
• 作为试剂：
  描述：

  (2S,4R)-1-Boc-2-氨基甲酰基-4-羟基吡咯烷 、 三氟乙酸酐 在 氩 、 水 、 乙酸乙酯 、 Brine 、 盐酸 、 sodium hydroxide 、 Sodium sulfate-III 、 (2S,4R)-1-Boc-2-氰基-4-羟基吡咯烷 作用下， 以 吡啶 为溶剂， 以to obtain the title compound (2S,4R)-tert-butyl 2-cyano-4-hydroxypyrrolidine-1-carboxylate 13d (49.7 g, yield 73%) as a brown oil的产率得到(2S,4R)-1-Boc-2-氰基-4-羟基吡咯烷
  参考文献：
  名称：

  Dicycloazaalkane derivates, preparation processes and medical uses thereof

  摘要：

  本发明涉及一种新的二环氮杂烷衍生物，其通式表示为(I)，以及制备方法、含有它们的制药组合物，以及用于治疗特别是二肽基肽酶抑制剂（DPP-IV）的用途，其中通式(I)的每个取代基如规范中定义。

  公开号：

  US08304411B2

文献信息

• [EN] NEW PYRROLIDINE-2-CARBOXYLIC ACID DERIVATIVES FOR TREATING PAIN AND PAIN RELATED CONDITIONS<br/>[FR] NOUVEAUX DÉRIVÉS D'ACIDE PYRROLIDINE-2-CARBOXYLIQUE POUR LE TRAITEMENT DE LA DOULEUR ET D'ÉTATS PATHOLOGIQUES ASSOCIÉS À LA DOULEUR
  申请人：ESTEVE PHARMACEUTICALS SA

  公开号：WO2020120539A1

  公开（公告）日：2020-06-18

  The present invention relates to new compounds that show pharmacological dual activity towards the subunit α2δ of voltage-gated calcium channels (VGCC), especially the α2δ-1 subunit of voltage-gated calcium channels, and the µ-opiod receptor (MOR or mu-opioid). The invention is also related to the process for the preparation of said compounds as well as to compositions comprising them, and to their use as medicaments (formula (I)).

  本发明涉及显示对电压门控钙通道（VGCC）的α2δ亚基，特别是电压门控钙通道的α2δ-1亚基，以及µ-阿片受体（MOR或μ-阿片）具有药理双重活性的新化合物。该发明还涉及所述化合物的制备过程，以及包含它们的组合物，以及它们作为药物的用途（公式（I））。
• Methods for Production of Optically Active Fluoropyrrolidine Derivatives
  申请人：Umemoto Teruo

  公开号：US20100174096A1

  公开（公告）日：2010-07-08

  Useful industrial methods for producing optically active fluoropyrrolidine derivatives as useful fluorinated intermediates are disclosed.

  揭示了用于生产光学活性氟吡咯烷衍生物的有用工业方法，作为有用的氟化中间体。
• Decarboxylative Cyanation of Aliphatic Carboxylic Acids via Visible-Light Flavin Photocatalysis
  作者：Nieves P. Ramirez、Burkhard König、Jose C. Gonzalez-Gomez

  DOI：10.1021/acs.orglett.9b00064

  日期：2019.3.1

  An operationally simple method is disclosed for the decarboxylative cyanation of aliphatic carboxylic acids at room temperature. Riboflavin tetraacetate, which is an inexpensive organic photocatalyst, promotes the oxidation of carboxylic acids upon visible-light activation. After decarboxylation, the generated radicals are trapped by TsCN, yielding the desired nitriles without any further additive

  公开了在室温下用于脂族羧酸的脱羧氰化的操作简单的方法。核黄素四乙酸酯是一种廉价的有机光催化剂，可在可见光激活时促进羧酸的氧化。脱羧后，在氧化还原中性过程中，生成的自由基被TsCN捕获，得到所需的腈，而无需任何其他添加剂。重要的是，该协议可以适应流量条件。
• Room temperature decarboxylative cyanation of carboxylic acids using photoredox catalysis and cyanobenziodoxolones: a divergent mechanism compared to alkynylation
  作者：Franck Le Vaillant、Matthew D. Wodrich、Jérôme Waser

  DOI：10.1039/c6sc04907a

  日期：——

  The one-step conversion of aliphatic carboxylic acids to the corresponding nitriles has been accomplished via the merger of visible light mediated photoredox and cyanobenziodoxolones (CBX) reagents. The reaction proceeded in high yields with natural and non-natural α-amino and α-oxy acids, affording a broad scope of nitriles with excellent tolerance of the substituents in the α position. The direct

  通过合并可见光介导的光氧化还原和氰基苯并酮（CBX）试剂，实现了脂肪族羧酸一步转化为相应的腈。天然和非天然 α-氨基酸和 α-含氧酸的反应以高产率进行，提供了广泛的腈类，并且对 α 位取代基具有优异的耐受性。还实现了二肽和药物前体的直接氰化。通过计算和实验研究了脱羧氰化的机理，并与之前开发的炔基化反应进行了比较。发现炔基化有利于直接自由基加成，而 CBX 进一步氧化成碳阳离子和氰化物加成似乎更有利于氰化。与通常假设的加成消除过程相反，提出了自由基与 EBX 试剂反应的协调机制。
• Compounds
  申请人：Aranyl Peter

  公开号：US20050153973A1

  公开（公告）日：2005-07-14

  Heterocyclic amides useful as inhibitors of dipeptylpeptidase-IV (DPP-IV) enzyme, process for the preparation thereof and intermediates therefore.

  杂环酰胺可用作二肽基肽酶-IV（DPP-IV）酶的抑制剂，其制备方法及其中间体。