(4R,5S,1'S)-1-(N-butyloxycarbonylprolyl)-4-hydroxyl-5-methylpyrrolidin-2-one | 1241920-89-7

• 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: (4R,5S,1'S)-1-(N-butyloxycarbonylprolyl)-4-hydroxyl-5-methylpyrrolidin-2-one
• 英文别名: tert-butyl (2S)-2-[(2S,3R)-3-hydroxy-2-methyl-5-oxopyrrolidine-1-carbonyl]pyrrolidine-1-carboxylate
• CAS: 1241920-89-7
• 化学式: C₁₅H₂₄N₂O₅
• 分子量: 312.366
• InChiKey: UHJJCEYXXALWSM-GARJFASQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  87.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4R,5S,1'S)-1-(N-butyloxycarbonylprolyl)-4-hydroxyl-5-methylpyrrolidin-2-one 在 4-二甲氨基吡啶 、 二碳酸二叔丁酯 作用下， 以 二氯甲烷 为溶剂， 以71%的产率得到(5S,1'S)-1-(N-tert-butyloxycarbonylprolyl)-5-methylpyrrol-2(5H)-one
  参考文献：
  名称：

  N-Benzyloxymalimide for an easy access to 5-alkyl-3-pyrrolin-2-ones: asymmetric synthesis of the mixed imide substructure of the potent immunosuppressant microcolin B

  摘要：

  O-Benzyl-N-benzyloxymalimide 12 has been synthesized as a useful variant of the chiral building blocks 9. The advantage of the malimide 12 over 9 was demonstrated by mild and high-yielding reductive N-deprotection of N-benzyloxylactams 18a-i to give a series of (4R,5S)-5-alkyl-4-hydroxy-pyrrolidin-2-ones, which are key intermediates for the asymmetric synthesis of pyrrolidines, pyrrolizidines, and indolizidines, as well as beta-hydroxy gamma-amino acids. Lactam ent-11a has been applied to the synthesis of the mixed imide 25, a key intermediate for the total synthesis of microcolin B, which also demonstrated that lactam ent-11a or 11a can serve as a latent form of the 5-methyl-3-pyrrolin-2-one substructure of majusculamide D 4, deoxymajusculamide D, and the jamaicamides A-C. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.04.063
• 作为产物：
  描述：

  (4R,5S,1'S)-4-benzyloxy-1-(N-butyloxycarbonylprolyl)-5-methylpyrrolidin-2-one 在 甲酸 、 palladium 10% on activated carbon 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以81%的产率得到(4R,5S,1'S)-1-(N-butyloxycarbonylprolyl)-4-hydroxyl-5-methylpyrrolidin-2-one
  参考文献：
  名称：

  N-Benzyloxymalimide for an easy access to 5-alkyl-3-pyrrolin-2-ones: asymmetric synthesis of the mixed imide substructure of the potent immunosuppressant microcolin B

  摘要：

  O-Benzyl-N-benzyloxymalimide 12 has been synthesized as a useful variant of the chiral building blocks 9. The advantage of the malimide 12 over 9 was demonstrated by mild and high-yielding reductive N-deprotection of N-benzyloxylactams 18a-i to give a series of (4R,5S)-5-alkyl-4-hydroxy-pyrrolidin-2-ones, which are key intermediates for the asymmetric synthesis of pyrrolidines, pyrrolizidines, and indolizidines, as well as beta-hydroxy gamma-amino acids. Lactam ent-11a has been applied to the synthesis of the mixed imide 25, a key intermediate for the total synthesis of microcolin B, which also demonstrated that lactam ent-11a or 11a can serve as a latent form of the 5-methyl-3-pyrrolin-2-one substructure of majusculamide D 4, deoxymajusculamide D, and the jamaicamides A-C. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.04.063

文献信息

• N-Benzyloxymalimide for an easy access to 5-alkyl-3-pyrrolin-2-ones: asymmetric synthesis of the mixed imide substructure of the potent immunosuppressant microcolin B
  作者：Zhao-Bao Ye、Jie Chen、Wei-Hua Meng、Pei-Qiang Huang

  DOI：10.1016/j.tetasy.2010.04.063

  日期：2010.4

  O-Benzyl-N-benzyloxymalimide 12 has been synthesized as a useful variant of the chiral building blocks 9. The advantage of the malimide 12 over 9 was demonstrated by mild and high-yielding reductive N-deprotection of N-benzyloxylactams 18a-i to give a series of (4R,5S)-5-alkyl-4-hydroxy-pyrrolidin-2-ones, which are key intermediates for the asymmetric synthesis of pyrrolidines, pyrrolizidines, and indolizidines, as well as beta-hydroxy gamma-amino acids. Lactam ent-11a has been applied to the synthesis of the mixed imide 25, a key intermediate for the total synthesis of microcolin B, which also demonstrated that lactam ent-11a or 11a can serve as a latent form of the 5-methyl-3-pyrrolin-2-one substructure of majusculamide D 4, deoxymajusculamide D, and the jamaicamides A-C. (C) 2010 Elsevier Ltd. All rights reserved.