(2R,4S)-tert-butyl-2-methyl-4-((methylsulfonyl)oxy)pyrrolidine-1-carboxylate | 874883-03-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (2R,4S)-tert-butyl-2-methyl-4-((methylsulfonyl)oxy)pyrrolidine-1-carboxylate
• 英文别名: tert-butyl (2R,4S)-4-(methanesulfonyloxy)-2-methylpyrrolidine-1-carboxylate；tert-butyl (2R,4S)-2-methyl-4-methylsulfonyloxypyrrolidine-1-carboxylate
• CAS: 874883-03-1
• 化学式: C₁₁H₂₁NO₅S
• 分子量: 279.357
• InChiKey: UJMCAWBIYLOHPV-BDAKNGLRSA-N

物化性质

• 沸点：
  397.7±31.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  81.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,4S)-tert-butyl-2-methyl-4-((methylsulfonyl)oxy)pyrrolidine-1-carboxylate 在 sodium azide 、 dicyclohexyl (2’,4’,6-triisopropyl-[1,1’-biphenyl]-2-yl)phosphine 、 palladium on activated charcoal 、 氢气 、 caesium carbonate 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 20.0~90.0 ℃ 、101.33 kPa 条件下， 反应 18.0h， 生成 (2R,4R)-tert-butyl-4-((4-cyanopyridin-2-yl)amino)-2-methylpyrrolidine-1-carboxylate
  参考文献：
  名称：

  [EN] PYRROLIDINE OREXIN RECEPTOR ANTAGONISTS
  [FR] COMPOSÉS PYRROLIDINE EN TANT QU'ANTAGONISTES DU RÉCEPTEUR DE L'HYPOCRÉTINE

  摘要：

  本发明涉及对促进素受体的拮抗剂吡咯烷化合物。本发明还涉及所述化合物在潜在的治疗或预防涉及促进素受体的神经和精神疾病和疾病中的用途。本发明还涉及包含这些化合物的组合物。本发明还涉及这些组合物在潜在的预防或治疗涉及促进素受体的疾病中的用途。

  公开号：

  WO2016095204A1
• 作为产物：
  描述：

  (2R,4R)-tert-butyl 2-methyl-4-(tosyloxy)pyrrolidine-1-carboxylate 在 sodium hydroxide 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 7.5h， 生成 (2R,4S)-tert-butyl-2-methyl-4-((methylsulfonyl)oxy)pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Direct Asymmetric anti-Mannich-Type Reactions Catalyzed by a Designed Amino Acid

  摘要：

  The development of catalysts for Mannich-type reactions that afford anti-products with excellent diastereo- and enantioselectivities under mild conditions and low catalyst loadings (1-5 mol %) is reported. Based on principles gained from the study of (S)-proline-catalyzed Mannich-type reactions that afford enantiomerically enriched syn-products, (3R,5R)-5-methyl-3-pyrrolidinecarboxylic acid (RR35) has been designed to catalyze the direct enantioselective anti-selective Mannich-type reactions. Computational studies of the above reaction using HF/6-31G* level of theory suggested that this design would be highly effective. The catalyst was subsequently synthesized and studied in organocatalytic Mannich-type reactions between unmodified aldehydes and N-PMP-protected alpha-imino esters. In accord with the design principles and in quantitative agreement with the theoretical predictions, reactions catalyzed by this catalyst afforded anti-products in good yields with excellent diastereo- and enantioselectivities (anti:syn 94:6 to 98:2, >97 to >99% ee).

  DOI：

  10.1021/ja056984f

文献信息

• TRANS-3,5-DISUBSTITUTEDPYRROLIDINE: ORGANOCATALYST FOR anti-MANNICH REACTIONS
  申请人：Tanaka Fujie

  公开号：US20070117986A1

  公开（公告）日：2007-05-24

  A compound of Formula I is disclosed, in which R is a substituent containing a hydrogen bond-forming atom within three atoms from the ring carbon to which the substituent is bonded; X is CH 2 , O, S or NR 1 , wherein R 1 is a hydrocarbyl group or an amino-protecting group having one to about 18 carbon atoms; R 2 is hydrido or a hydrocarbyl group containing one to about twelve carbon atoms; and R 3 is hydrido or methyl, but both R 2 and R 3 are not hydrido when X is CH 2 A molecule of Formula I and those in which R 2 and R 3 can both be hydrido (Formula X) functions as a catalyst in a Mannich reaction to asymmetrically form β-aminoaldehyde or β-aminoketone diastereomeric products having two chiral centers on adjacent carbon atoms and in which the anti-diastereomers are in excess over the syn-diastereomers. Methods for carrying out those syntheses are also disclosed.

  披露了一种公式I的化合物，其中R是含有一个在距离与亚基连接的环碳三个原子以内的氢键形成原子的取代基；X是CH2，O，S或NR1，其中R1是一个含有一个到约18个碳原子的烃基团或一个氨基保护基团；R2是氢化物或含有一个到约十二个碳原子的烃基团；R3是氢化物或甲基，但是当X是CH2时，R2和R3不能都是氢化物。公式I的分子以及其中R2和R3都可以是氢化物（公式X）的分子，在曼尼希反应中作为催化剂，非对称地形成具有相邻碳原子上的两个手性中心的β-氨基醛或β-氨基酮对映异构体产品，并且反式对映异构体过剩于顺式对映异构体。还披露了进行那些合成的方法。
• 6 SUBSTITUTED 2- HETEROCYCLYLAMINO PYRAZINE COMPOUNDS AS CHK-1 INHIBITORS
  申请人：Braganza John Frederick

  公开号：US20110144084A1

  公开（公告）日：2011-06-16

  The present invention is directed to compounds of formula (I), and pharmaceutically acceptable salts thereof, their synthesis, and their use as CHK-1 inhibitors.

  本发明涉及式（I）化合物及其药学上可接受的盐，它们的合成以及它们作为CHK-1抑制剂的用途。
• 6 SUBSTITUTED 2-HETEROCYCLYLAMINO PYRAZINE COMPOUNDS AS CHK-1 INHIBITORS
  申请人：Pfizer Inc.

  公开号：EP2328890B1

  公开（公告）日：2012-01-25
• PYRROLIDINE OREXIN RECEPTOR ANTAGONISTS
  申请人：Merck Sharp & Dohme Corp.

  公开号：US20170342052A1

  公开（公告）日：2017-11-30

  The present invention is directed to pyrrolidine compounds which are antagonists of orexin receptors. The present invention is also directed to uses of the compounds described herein in the potential treatment or prevention of neurological and psychiatric disorders and diseases in which orexin receptors are involved. The present invention is also directed to compositions comprising these compounds. The present invention is also directed to uses of these compositions in the potential prevention or treatment of such diseases in which orexin receptors are involved.
• COMBINATION OF CHIMERIC ANTIGEN RECEPTOR THERAPY AND AMINO PYRIMIDINE DERIVATIVES
  申请人：Angst Daniela

  公开号：US20180140602A1

  公开（公告）日：2018-05-24

  The invention provides compositions and methods for treating diseases associated with expression of CD19, e.g., by administering a recombinant T cell comprising the CD19 CAR as described herein, in combination with a BTK inhibitor, e.g., an amino pyrimidine derivative described herein. The invention also provides kits and compositions described herein.