(4S,1'S)-4-benzyloxymethyl-1-(1'-phenylethyl)pyrrolidin-2-one | 641634-56-2

• 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: (4S,1'S)-4-benzyloxymethyl-1-(1'-phenylethyl)pyrrolidin-2-one
• 英文别名: (S)-4-((benzyloxy)methyl)-1-((S)-1-phenylethyl)pyrrolidin-2-one；(4S)-1-[(1S)-1-phenylethyl]-4-(phenylmethoxymethyl)pyrrolidin-2-one
• CAS: 641634-56-2
• 化学式: C₂₀H₂₃NO₂
• 分子量: 309.408
• InChiKey: ASYJFTXTXKZSKW-WMZOPIPTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4S,1'S)-4-benzyloxymethyl-1-(1'-phenylethyl)pyrrolidin-2-one 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 氯甲酸氯乙酯 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 10.16h， 生成 (3S,4S)-3-benzyloxymethyl-1-(tert-butoxycarbonyl)-4-(2'-methylprop-1'-yl)pyrrolidine
  参考文献：
  名称：

  Synthesis of a conformationally restricted analog of pregabalin by stereoselective alkylation of a chiral pyrrolidin-2-one

  摘要：

  The 4-benzyloxymethyl pyrrolidin-2-one, 5, was alkylated leading to 3,4-trans-disubstituted pyrrolidin-2-one 6 in good yield and total diastereoselection, as shown by H-1 NMR data and NOE experiments. After reduction of the carbonyl group to give the trans-3,4-disubstituted pyrrolidine 7, and removal of the chiral auxiliary, followed by protection of the nitrogen with t-Boc group, the corresponding N-protected pyrrolidine, 8 was obtained. The cleavage of the benzyl ether moiety, followed by oxidation of the hydroxy function, gave in good yield the corresponding pyrrolidine carboxylic acid 2, a restricted analog of pregabalin. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00599-8
• 作为产物：
  描述：

  methyl 5-oxo-1-((S)-1-phenylethyl)pyrrolidine-3-(S)-carboxylate 在 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 4.17h， 生成 (4S,1'S)-4-benzyloxymethyl-1-(1'-phenylethyl)pyrrolidin-2-one
  参考文献：
  名称：

  通过手性γ-内酰胺的亲电胺化，在难于构象的α-甲基高丝氨酸类似物的合成中进行高度稳定的阻转异构体

  摘要：

  从手性保护的4-羟甲基吡咯烷酮-2-酮开始，利用立体选择性亲电试剂制备了难以捉摸的α-甲基高丝氨酸的3,4-反式-3,3,4-三取代的等排体，它们被束缚在γ-内酰胺环上。胺化。这些反应导致了新型的阻转异构体的分离和表征，这种阻转异构体在室温下非常稳定，可通过新型的非还原性N–N键断裂反应直接转化为所需的产物。

  DOI：

  10.1007/s00726-015-2100-4

文献信息

• Highly stable atropisomers by electrophilic amination of a chiral γ-lactam within the synthesis of an elusive conformationally restricted analogue of α-methylhomoserine
  作者：Paolo Amabili、Adolfo Amici、Annafelicia Civitavecchia、Beatrice Maggiore、Mario Orena、Samuele Rinaldi、Alessandra Tolomelli

  DOI：10.1007/s00726-015-2100-4

  日期：2016.2

  tethered on a γ-lactam ring, were prepared exploiting stereoselective electrophilic aminations. These reactions led to the isolation and characterization of a novel type of atropisomers, exceedingly stable at room temperature, that were directly converted to the desired products by a novel non-reductive N–N bond cleavage reaction.

  从手性保护的4-羟甲基吡咯烷酮-2-酮开始，利用立体选择性亲电试剂制备了难以捉摸的α-甲基高丝氨酸的3,4-反式-3,3,4-三取代的等排体，它们被束缚在γ-内酰胺环上。胺化。这些反应导致了新型的阻转异构体的分离和表征，这种阻转异构体在室温下非常稳定，可通过新型的非还原性N–N键断裂反应直接转化为所需的产物。
• Synthesis of a conformationally restricted analog of pregabalin by stereoselective alkylation of a chiral pyrrolidin-2-one
  作者：Roberta Galeazzi、Gianluca Martelli、Giovanna Mobbili、Mario Orena、Samuele Rinaldi

  DOI：10.1016/s0957-4166(03)00599-8

  日期：2003.10

  The 4-benzyloxymethyl pyrrolidin-2-one, 5, was alkylated leading to 3,4-trans-disubstituted pyrrolidin-2-one 6 in good yield and total diastereoselection, as shown by H-1 NMR data and NOE experiments. After reduction of the carbonyl group to give the trans-3,4-disubstituted pyrrolidine 7, and removal of the chiral auxiliary, followed by protection of the nitrogen with t-Boc group, the corresponding N-protected pyrrolidine, 8 was obtained. The cleavage of the benzyl ether moiety, followed by oxidation of the hydroxy function, gave in good yield the corresponding pyrrolidine carboxylic acid 2, a restricted analog of pregabalin. (C) 2003 Elsevier Ltd. All rights reserved.