[(3R,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidin-3-yl]methanol | 604798-43-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(3R,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidin-3-yl]methanol
• 英文别名: (3R,4R)-(1-benzyloxycarbonyl-4-hydroxypyrrolidin-3-yl)methanol；benzyl (3R,4R)-3-hydroxy-4-(hydroxymethyl)pyrrolidine-1-carboxylate
• CAS: 604798-43-8
• 化学式: C₁₃H₁₇NO₄
• 分子量: 251.282
• InChiKey: WOMQTKDTCNPUAH-NEPJUHHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  70
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(3R,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidin-3-yl]methanol 在 sodium azide 、 四溴化碳 、 三苯基膦 作用下， 以 DMF (N,N-dimethyl-formamide) 、 二氯甲烷 为溶剂， 反应 27.0h， 生成 (3R,4R)-3-azidomethyl-1-benzyloxycarbonyl-4-hydroxypyrrolidine
  参考文献：
  名称：

  10-(3-CYCLOPROPYLAMINOMETHYL-1-PYRROLIDINYL)PYRIDOBENZOXAZINECARBOXYLIC ACID DERIVATIVE EFFECTIVE AGAINST RESISTANT BACTERIA

  摘要：

  公开号：

  EP1486500B1
• 作为产物：
  描述：

  (3R,4S)-deoxy-3-C-(N-benzyloxycarbonyl)aminomethyl-1,2:5,6-di-o-isopropylidene-α-d-allofuranose 在 盐酸 、 水 、 三乙基硅烷 、 三氟化硼乙醚 、 sodium tetrahydroborate 、 sodium periodate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 [(3R,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidin-3-yl]methanol
  参考文献：
  名称：

  7-(4-SUBSTITUTED 3- CYCLOPROPYLAMINOMETHYL-1- PYRROLIDINYL) Q UINOLONECARBOXYLIC ACID DERIVATIVE

  摘要：

  公开号：

  EP1666477B1

文献信息

• 10-(3-cyclopropylaminomethyl-1-pyrrolidinyl)pyridobenzoxazinecarboxylic acid derivative effective against resistant bacterium
  申请人：Asahina Yoshikazu

  公开号：US20050182052A1

  公开（公告）日：2005-08-18

  A compound as represented by the general formula (I) shown below exhibits high antibacterial activity against gram-positive bacteria, in particular, such drug-resistant bacteria as mRNA, PRSP and VRE: wherein R1 is a methyl group, a fluoromethyl group, a methoxymethyl group, an acetoxymethyl group, a hydroxymethyl group or a methylene; R2 is a hydrogen atom, a lower alkyl group having 1 to 3 carbon atoms, or a pharmaceutically acceptable cation and an ester of a prodrug; R3 is a hydrogen atom or a halogen atom; R4 is a hydrogen atom, a lower alkyl group having 1 to 3 carbon atoms, a fluoromethyl group, a trifluoromethyl group or a fluorine atom; and R5 is a hydrogen atom or a fluorine atom, with exceptions where R1 is a methyl group, R4 and R5 are at the same time a hydrogen atom, and R3 is a fluorine atom.

  下列通式（I）所代表的化合物对革兰氏阳性细菌表现出高度的抗菌活性，特别是对那些耐药菌如mRNA、PRSP和VRE： 其中，R1是甲基、氟甲基、甲氧甲基、乙酰氧甲基、羟甲基或亚甲基；R2是氢原子、具有1至3个碳原子的低烷基或药学上可接受的阳离子和前药的酯；R3是氢原子或卤素原子；R4是氢原子、具有1至3个碳原子的低烷基、氟甲基、三氟甲基或氟原子；R5是氢原子或氟原子，除非R1是甲基、R4和R5同时为氢原子，且R3是氟原子的情况。
• 7-(4-Substituted-3-cyclopropylaminomethyl-1 pyrrolidinyl) quinolonecarboxylic acid derivative
  申请人：Asahina Yoshikazu

  公开号：US20060281779A1

  公开（公告）日：2006-12-14

  OBJECT To provide novel quinolonecarboxylic acid compounds serving as safe, strong antibacterial agents that are effective against drug-resistant bacteria that are less susceptible to conventional antibacterial agents. SOLVING MEANS There are provided 7-(4-substituted-3-cyclopropylaminomethylpyrrolidinyl)quinolonecarboxylic acid derivatives (such as 1-cyclopropyl-7-[(3S,4S)-3-cyclopropylaminomethyl-4-fluoro-1-pyrrolidinyl]-6-fluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid) that exhibit strong antibacterial activity against gram-positive bacteria, such as MRSA, PRSP and VRE, while being safe. The compounds are shown by the following general formula (I):

  目的：提供新型喹诺酮羧酸化合物，作为安全、强效的抗菌剂，对耐药菌有良好的抗菌效果，而且对传统抗菌剂的抗性较低。 解决方法：提供7-(4-取代的3-环丙氨甲基吡咯烷基)喹诺酮羧酸衍生物（例如1-环丙基-7-[(3S,4S)-3-环丙氨甲基-4-氟-1-吡咯烷基]-6-氟-1,4-二氢-8-甲氧基-4-氧代-3-喹啉羧酸），对革兰氏阳性菌（如MRSA、PRSP和VRE）表现出强效的抗菌活性，同时具有安全性。这些化合物的通用式如下（I）：
• Process for producing 3,4-disubstituted pyrrolidine derivative and production intermediate thereof
  申请人：Gotoh Takayuki

  公开号：US20100056805A1

  公开（公告）日：2010-03-04

  An industrially advantageous process for the production of (3R,4S)-3-cyclopropylaminomethyl-4-fluoropyrrolidine or an enantiomer thereof that is useful as an intermediate for the production of novel antimicrobial agents 10-(3-cyclopropylaminomethyl-4-fluoropyrrolidinyl)pyridobenzoxazine carboxylic acid derivatives. Highly stereoselective asymmetric hydrogenation of 1-protected-4-alkoxycarbonyl-3-oxopyrrolidine, followed by ester hydrolysis, followed by amidation with cyclopropylamine gives crude crystals. The crude crystals are purified by recrystallization to give a novel compound (3R,4S)- 1 -protected-3-cyclopropylcarbamoyl-4-hydroxypyrrolidine or an enantiomer thereof at high optical purity. The use of these intermediates enables industrial production of high-quality products of (3R,4S)-3-cyclopropylaminomethyl-4-fluoropyrrolidine or an enantiomer thereof. The process is highly simple and can produce the desired products at high purity and stable yields.

  这是一种工业上有利的生产过程，用于生产（3R,4S）-3-环丙氨基甲基-4-氟吡咯烷或其对映体，该对映体可用作新型抗微生物剂10-（3-环丙氨基甲基-4-氟吡咯烷基）吡啶苯并噁唑羧酸衍生物的中间体。高度立体选择性的不对称氢化1-保护-4-烷氧羰基-3-酮吡咯烷，随后进行酯水解，然后与环丙胺酰胺化，得到粗晶体。通过重结晶纯化粗晶体，得到一种新化合物（3R,4S）-1-保护-3-环丙氨基甲酰基-4-羟基吡咯烷或其对映体，光学纯度高。使用这些中间体可以工业化生产高质量的（3R,4S）-3-环丙氨基甲基-4-氟吡咯烷或其对映体产品。该过程非常简单，可以高纯度和稳定产量地生产所需的产品。
• 7- (4-substituted-3-cyclopropylaminomethyl-1-pyrrolidinyl) quinolonecarboxylic acid derivative
  申请人：Kyorin Pharmaceutical Co., Ltd.

  公开号：US08106072B2

  公开（公告）日：2012-01-31

  Object To provide novel quinolinecarboxylic acid compounds serving as safe, strong antibacterial agents that are effective against drug-resistant bacteria that are less susceptible to conventional antibacterial agents. Solving Means There are provided 7-(4-substituted-3-cyclopropylaminomethylpyrrolidinyl)quinolonecarboxylic acid derivatives (such as 1-cyclopropyl-7-[(3S,4S)-3-cyclopropylaminomethyl-4-fluoro-1-pyrrolidinyl]-6-fluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid) that exhibit strong antibacterial activity against gram-positive bacteria, such as MRSA, PRSP and VRE, while being safe. The compounds are shown by the following general formula (I):

  目标：提供新型喹诺酸类化合物，作为安全、强效的抗菌剂，对耐药细菌具有有效作用，且对常规抗菌剂的敏感性较低。 解决方法：提供7-(4-取代的3-环丙氨甲基吡咯啉基)喹诺酸衍生物（例如1-环丙基-7-[(3S,4S)-3-环丙氨甲基-4-氟-1-吡咯啉基]-6-氟-1,4-二氢-8-甲氧基-4-氧代-3-喹诺酸），对革兰氏阳性菌（如MRSA、PRSP和VRE）表现出强效的抗菌活性，同时具有安全性。这些化合物由以下通式（I）表示：
• 7- (4-substituted-3-cyclopropylaminomethyl-1-pyrrolidinyl) quinolonecarboxylic acid derivative technical field
  申请人：Asahina Yoshikazu

  公开号：US20090176824A1

  公开（公告）日：2009-07-09

  Object To provide novel quinolonecarboxylic acid compounds serving as safe, strong antibacterial agents that are effective against drug-resistant bacteria that are less susceptible to conventional antibacterial agents. Solving Means There are provided 7-(4-substituted-3-cyclopropylaminomethylpyrrolidinyl)quinolonecarboxylic acid derivatives (such as 1-cyclopropyl-7-[(3S,4S)-3-cyclopropylaminomethyl-4-fluoro-1-pyrrolidinyl]-6-fluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid) that exhibit strong antibacterial activity against gram-positive bacteria, such as MRSA, PRSP and VRE, while being safe. The compounds are shown by the following general formula (I):

  目标 提供新型喹诺酸类化合物，作为安全、强效的抗菌剂，对耐药菌有良好的抗菌效果，对传统抗菌剂不敏感。 解决方法 提供7-(4-取代-3-环丙氨甲基吡咯烷基)喹诺酸衍生物（如1-环丙基-7-[(3S,4S)-3-环丙氨甲基-4-氟-1-吡咯烷基]-6-氟-1,4-二氢-8-甲氧基-4-氧代-3-喹啉羧酸），对革兰阳性菌有强效的抗菌活性，如MRSA、PRSP和VRE，同时具有安全性。这些化合物的一般式如下（I）：