1-benzyl 3-ethyl (3S,4R)-4-hydroxypyrrolidine-1,3-dicarboxylate | 949495-11-8

• 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: 1-benzyl 3-ethyl (3S,4R)-4-hydroxypyrrolidine-1,3-dicarboxylate
• 英文别名: (3S,4R)-1-Benzyl 3-ethyl 4-hydroxypyrrolidine-1,3-dicarboxylate；1-O-benzyl 3-O-ethyl (3S,4R)-4-hydroxypyrrolidine-1,3-dicarboxylate
• CAS: 949495-11-8
• 化学式: C₁₅H₁₉NO₅
• 分子量: 293.32
• InChiKey: CBNVXCYLCGIIPD-STQMWFEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-benzyl 3-ethyl (3S,4R)-4-hydroxypyrrolidine-1,3-dicarboxylate 在 sodium hydroxide 、 乙醇 、 水 、 盐酸 作用下， 反应 1.0h， 生成 (3S,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidine-3-carboxylic acid
  参考文献：
  名称：

  PROCESS FOR PRODUCTION OF 3,4-DISUBSTITUTED PYRROLIDINE DERIVATIVE AND INTERMEDIATE FOR THE PRODUCTION

  摘要：

  公开号：

  EP1992613B1
• 作为产物：
  描述：

  N-Cbz-4-氧代-3-吡咯烷甲酸乙酯 在 [RuCl2(benzene)]2 、 (S)-binap 氢气 作用下， 以 二氯甲烷 为溶剂， 50.0~102.0 ℃ 、5.0 MPa 条件下， 反应 5.17h， 生成 1-benzyl 3-ethyl (3S,4R)-4-hydroxypyrrolidine-1,3-dicarboxylate
  参考文献：
  名称：

  PROCESS FOR PRODUCTION OF 3,4-DISUBSTITUTED PYRROLIDINE DERIVATIVE AND INTERMEDIATE FOR THE PRODUCTION

  摘要：

  公开号：

  EP1992613B1

文献信息

• METHOD FOR PRODUCING 3,4-DISUBSTITUTED PYRROLIDINE DERIVATIVE
  申请人：Araya Ichiro

  公开号：US20130217893A1

  公开（公告）日：2013-08-22

  The present invention provides an inexpensive and industrially advantageous method for producing an optically active form of an anti-(3S,4R)-3-alkylcarbamoyl-4-hydroxypyrrolidine derivative or it's enantiomer, which is a key intermediate for producing a high-quality optically active form of (3R,4S)-3-alkylaminomethyl-4-fluoropyrrolidine or it's enantiomer useful as an intermediate for producing pharmaceuticals. The present invention relates to a method for producing an optically active anti-(3S,4R)-4-hydroxypyrrolidine-3-carboxamide derivative, or it's enantiomer by carrying out asymmetric hydrogenation using an optically active catalyst of a 4-oxopyrrolidine-3-carboxamide derivative represented by the general formula (I). [in the formula (I), PG 1 represents a protective group for an amino group, and R 1 represents hydrogen, a C1 to C6 alkyl group which may be substituted, or a C3 to C8 cycloalkyl group which may be substituted].

  本发明提供了一种廉价且在工业上具有优势的方法，用于生产抗-(3S,4R)-3-烷基氨甲酰基-4-羟基吡咯烷衍生物或其对映体的光学活性形式，该衍生物是生产高质量光学活性形式的(3R,4S)-3-烷基氨甲基-4-氟吡咯烷或其对映体的关键中间体，可用作生产药物的中间体。本发明涉及一种通过使用由通式(I)表示的4-氧代吡咯烷-3-羧酰胺衍生物的光学活性催化剂进行不对称氢化来生产光学活性的抗-(3S,4R)-4-羟基吡咯烷-3-羧酰胺衍生物或其对映体的方法。【在通式(I)中，PG1代表氨基的保护基，R1代表氢、可被取代的C1至C6烷基或可被取代的C3至C8环烷基】。
• Process for Producing 3,4-Disubstituted Pyrrolidine Derivative and Production Intermediate Thereof
  申请人：Gotoh Takayuki

  公开号：US20090023935A1

  公开（公告）日：2009-01-22

  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.

  这是一种工业上优越的过程，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)吡啶并苯并噁嗪羧酸衍生物的中间体。高度立体选择性的不对称氢化1-保护的4-烷氧羰基-3-氧代吡咯烷，随后进行酯水解，然后与环丙氨基酰胺反应，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-保护的3-环丙氨基甲酰基-4-羟基吡咯烷或其对映体，其光学纯度高。使用这些中间体能够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。该过程非常简单，能够以高纯度和稳定的产率生产所需的产品。
• 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。
• EP1992613A1
  申请人：——

  公开号：EP1992613A1

  公开（公告）日：2008-11-19
• US7667049B2
  申请人：——

  公开号：US7667049B2

  公开（公告）日：2010-02-23