(2S,5S)-5-Butylproline tert-butyl ester | 95513-48-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,5S)-5-Butylproline tert-butyl ester
• 英文别名: (2S)-cis-5-butylproline tert-butyl ester；(2S,5S)-tert-butyl 5-butyl-pyrrolidine-2-carboxylate；tert-butyl (2S,5S)-5-butylpyrrolidine-2-carboxylate
• CAS: 95513-48-7
• 化学式: C₁₃H₂₅NO₂
• 分子量: 227.347
• InChiKey: OJDQGHNTALCMSZ-QWRGUYRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,5S)-5-Butylproline tert-butyl ester 在 calcined K₂CO₃ 、 水 、 溶剂黄146 作用下， 以 丙醇 、 乙醚 、 乙腈 为溶剂， 反应 35.5h， 生成 (2S)-cis-1-benzyl-5-butyl-2-(1-hydroxyheptyl)pyrrolidine
  参考文献：
  名称：

  .alpha.-Amino acids as chiral educts for asymmetric products. Chirospecific syntheses of the 5-butyl-2-heptylpyrrolidines from glutamic acid

  摘要：

  DOI：

  10.1021/jo00208a016
• 作为产物：
  描述：

  L-α-tert-butyl γ-methyl N-(9-(9-phenylfluorenyl))glutamate 在 palladium on activated charcoal lithium hydroxide 、 正丁基锂 、 氢气 、 六甲基二硅氮烷 作用下， 以 四氢呋喃 、 甲醇 、 溶剂黄146 为溶剂， 反应 24.0h， 生成 (2S,5S)-5-Butylproline tert-butyl ester
  参考文献：
  名称：

  Synthesis of enantiopure .delta.-oxo .alpha.-amino esters and prolines via acylation of N-(phenylfluorenyl)glutamate enolates

  摘要：

  Acylation of the lithium gamma-enolate of alpha-tert-butyl gamma-methyl N-[9-(9-phenylfluorenyl)]glutamate (1) with different acid chlorides provides beta-keto esters 2. Selective gamma-ester hydrolysis and decarboxylation furnishes good yields of enantiomerically pure delta-oxo alpha-amino esters 3 possessing primary, secondary, and tertiary alkyl, as well as aromatic delta-substituents. Acylation of 1 with methyl oxalyl chloride is followed by condensation of the ketone and amine of 2 to give N-(PhF1)-DELTA2-pyrroline triester 4 in 75% yield. Palladium-catalyzed hydrogenation of (2S)-tert-butyl 4-oxo-2-(N-(PhFl)amino)nonanoate (3f) yields >99.5% enantiopure (2S,5S)-5-butylproline tert-butyl ester (5), an intermediate in the synthesis of 2,5-dialkylpyrrolidine alkaloids.

  DOI：

  10.1021/jo00075a046

文献信息

• Application of asymmetric phase-transfer catalysis in the enantioselective synthesis of cis-5-substituted proline esters
  作者：Barry Lygo、Christopher Beynon、Michael C. McLeod、Claude-Eric Roy、Charles E. Wade

  DOI：10.1016/j.tet.2010.09.075

  日期：2010.11

  A simple, highly stereoselective three-step sequence for the enantioselective synthesis of cis-5-substituted praline esters is described. This sequence features an asymmetric PTC Michael addition, followed by acid catalysed imine exchange and catalytic hydrogenation. Application of this chemistry in the synthesis of the nonpeptide cholecystokinin antagonist (+)-RP-66803 11 is also described. (C) 2010 Elsevier Ltd. All rights reserved.
• .alpha.-Amino acids as chiral educts for asymmetric products. Chirospecific syntheses of the 5-butyl-2-heptylpyrrolidines from glutamic acid
  作者：Kazumi Shiosaki、Henry Rapoport

  DOI：10.1021/jo00208a016

  日期：1985.4
• Synthesis of enantiopure .delta.-oxo .alpha.-amino esters and prolines via acylation of N-(phenylfluorenyl)glutamate enolates
  作者：Houda H. Ibrahim、William D. Lubell

  DOI：10.1021/jo00075a046

  日期：1993.11

  Acylation of the lithium gamma-enolate of alpha-tert-butyl gamma-methyl N-[9-(9-phenylfluorenyl)]glutamate (1) with different acid chlorides provides beta-keto esters 2. Selective gamma-ester hydrolysis and decarboxylation furnishes good yields of enantiomerically pure delta-oxo alpha-amino esters 3 possessing primary, secondary, and tertiary alkyl, as well as aromatic delta-substituents. Acylation of 1 with methyl oxalyl chloride is followed by condensation of the ketone and amine of 2 to give N-(PhF1)-DELTA2-pyrroline triester 4 in 75% yield. Palladium-catalyzed hydrogenation of (2S)-tert-butyl 4-oxo-2-(N-(PhFl)amino)nonanoate (3f) yields >99.5% enantiopure (2S,5S)-5-butylproline tert-butyl ester (5), an intermediate in the synthesis of 2,5-dialkylpyrrolidine alkaloids.