(R)-3-(甲基氨基)吡咯烷-1-甲酸叔丁酯 | 199336-83-9

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 酯类氨基酸
• 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: (R)-3-(甲基氨基)吡咯烷-1-甲酸叔丁酯
• 中文别名: (R)-1-Boc-3-(甲氨基)吡咯烷
• 英文名称: tert-butyl (3R)-3-(methylamino)pyrrolidine-1-carboxylate
• 英文别名: (R)-tert-butyl 3-(methylamino)pyrrolidine-1-carboxylate；tert-butyl (R)-3-(methylamino)pyrrolidine-1-carboxylate
• CAS: 199336-83-9
• 化学式: C₁₀H₂₀N₂O₂
• 分子量: 200.281
• InChiKey: OKUCEQDKBKYEJY-MRVPVSSYSA-N

物化性质

• 沸点：
  269 ºC
• 密度：
  1.03
• 闪点：
  117 ºC

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温且干燥环境下使用。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: (R)-3-(Methylamino)pyrrolidine-1-carboxylic acid tert-butyl ester
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: (R)-3-(Methylamino)pyrrolidine-1-carboxylic acid tert-butyl ester
CAS number: 199336-83-9

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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, refrigerated.
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: C10H20N2O2
Molecular weight: 200.3

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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

制备方法与用途

应用

(R)-3-(甲基氨基)吡咯烷-1-甲酸叔丁酯可以作为有机合成中间体和医药中间体，主要用于实验室研发过程和化工生成过程中。

制备

将(R)-3-(甲基氨基)吡咯烷羧酸溶解于100 mL氢氧化钠水溶液中，随后依次加入200 mL四氢呋喃和250 g二碳酸二叔丁酯。控制pH值在8-9之间，反应12小时后，使用乙酸乙酯萃取两次，每次500 mL；再用水相用盐酸酸化至pH值为1-2，并进行三次乙酸乙酯萃取，每次也是500 mL。合并有机层并用饱和盐水洗涤两次，每次200 mL。最后，使用无水硫酸钠干燥12小时后过滤、浓缩结晶，在40-50℃下烘干，得到(R)-3-(甲基氨基)吡咯烷羧酸叔丁酯。

反应信息

• 作为反应物：
  描述：

  (R)-3-(甲基氨基)吡咯烷-1-甲酸叔丁酯 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 (R)-N-(1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyrrolidin-3-yl)-N-methyl-2-(trifluoromethyl)benzamide
  参考文献：
  名称：

  [EN] PYRROLOPYRIMIDINE COMPOUNDS AND USES THEREOF
  [FR] COMPOSÉS DE PYRROLOPYRIMIDINE ET LEURS UTILISATIONS

  摘要：

  公开了具有以下式（I）的吡咯吡嘧啶化合物，能够抑制JAK激酶，其中R1、R2和m的定义如描述中所述。还公开了含有所述吡咯吡嘧啶化合物的药物组合物，以及所述吡咯吡嘧啶化合物在治疗炎症性疾病和癌症等疾病或疾病中的用途。

  公开号：

  WO2012022265A1
• 作为产物：
  描述：

  tert-butyl (3R)-3-{[(2-nitrophenyl)sulfonyl]amino}pyrrolidine-1-carboxylate 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 17.0h， 生成 (R)-3-(甲基氨基)吡咯烷-1-甲酸叔丁酯
  参考文献：
  名称：

  发现了一种新型的双环化合物DS54360155，它是一种口服有效的止痛药，没有mu阿片类受体激动剂活性。

  摘要：

  我们合成了天然生物碱，可可定的衍生物，并在口服后在ddY小鼠中的乙酸诱导的扭体试验和福尔马林试验中评估了这些衍生物。结果，我们确定了（5 S）-6-甲基-1,3,4,5,6,8-六氢-7H-2,5-甲基[1,5]重氮基[7,8-b]吲哚-7-硫酸盐15a（DS54360155）具有独特的原始双环骨架，比可可啶具有更强的镇痛作用。此外，15a没有表现出μ阿片受体激动剂活性。

  DOI：

  10.1016/j.bmcl.2019.126748

文献信息

• [EN] INHIBITORS OF WDR5 PROTEIN-PROTEIN BINDING<br/>[FR] INHIBITEURS DE LA LIAISON PROTÉINE WDR5-PROTÉINE
  申请人：ONTARIO INST FOR CANCER RES (OICR)

  公开号：WO2017147700A1

  公开（公告）日：2017-09-08

  The present application is directed to compounds of Formula I: compounds comprising these compounds and their uses, for example as medicaments for the treatment of diseases, disorders or conditions mediated or treatable by inhibition of binding between WDR5 protein and its binding partners.

  本申请涉及到Formula I的化合物：包括这些化合物的化合物及其用途，例如作为治疗由于抑制WDR5蛋白与其结合伙伴之间结合而介导或可治疗的疾病、疾病或症状的药物。
• [EN] PROGRANULIN MODULATORS AND METHODS OF USING THE SAME<br/>[FR] MODULATEURS DE LA PROGRANULINE ET LEURS PROCÉDÉS D'UTILISATION
  申请人：ARKUDA THERAPEUTICS

  公开号：WO2020252222A1

  公开（公告）日：2020-12-17

  Provided herein are compounds that modulate progranulin and methods of using the compounds in progranulin-associated disorders, such as Frontotemporal dementia (FTD).

  本文件提供了调节颗粒蛋白的化合物及其在颗粒蛋白相关疾病中的使用方法，例如额颞痴呆（FTD）。
• FUSED QUADRACYCLIC COMPOUNDS, COMPOSITIONS AND USES THEREOF
  申请人：Tabomedex Biosciences, LLC

  公开号：US20170190713A1

  公开（公告）日：2017-07-06

  Provided herein are substituted fused quadracyclic compounds useful as inhibitors of MK2. The invention further provides pharmaceutical compositions of the compounds of the invention. The invention also provides medical uses of substituted fused quadracyclic compounds.

  本文提供了作为MK2抑制剂有用的替代融合四环化合物。本发明还提供了所述化合物的药物组合物。本发明还提供了替代融合四环化合物的医药用途。
• [EN] NEW COMPOUNDS FOR TREATMENT OF DISEASES RELATED TO DUX4 EXPRESSION<br/>[FR] NOUVEAUX COMPOSÉS POUR LE TRAITEMENT DE MALADIES LIÉES À L'EXPRESSION DE DUX4
  申请人：FACIO INTELLECTUAL PROPERTY B V

  公开号：WO2021105474A1

  公开（公告）日：2021-06-03

  The present invention relates to compounds for the treatment of diseases related to DUX4 expression, such as muscular dystrophies. It also relates to use of such compounds, or to methods of use of such compounds.

  本发明涉及用于治疗与DUX4表达相关疾病的化合物，如肌肉萎缩症。它还涉及使用这些化合物，或者使用这些化合物的方法。
• ALK5 INHIBITORS
  申请人：THERAVANCE BIOPHARMA R&D IP, LLC

  公开号：US20200188370A1

  公开（公告）日：2020-06-18

  The present disclosure provides inhibitors of activin receptor-like kinase 5 (ALK5). Also disclosed are methods to modulate the activity of ALK5 and methods of treatment of disorders mediated by ALK5.

  本公开提供抑制活性素受体样激酶5（ALK5）的抑制剂。还公开了调节ALK5活性的方法以及治疗由ALK5介导的疾病的方法。