(3S,4S,1'S)-4-benzyloxymethyl-3-(2''-methylprop-1''-yl)-1-(1'-phenylethyl)pyrrolidin-2-one | 641634-57-3

• 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: (3S,4S,1'S)-4-benzyloxymethyl-3-(2''-methylprop-1''-yl)-1-(1'-phenylethyl)pyrrolidin-2-one
• 英文别名: (3S,4S)-3-(2-methylpropyl)-1-[(1S)-1-phenylethyl]-4-(phenylmethoxymethyl)pyrrolidin-2-one
• CAS: 641634-57-3
• 化学式: C₂₄H₃₁NO₂
• 分子量: 365.516
• InChiKey: CRBDMHXCLRKBAJ-VJBMBRPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  (3S,4S,1'S)-4-benzyloxymethyl-3-(2''-methylprop-1''-yl)-1-(1'-phenylethyl)pyrrolidin-2-one 在 palladium on activated charcoal 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 甲酸 、 氯甲酸氯乙酯 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 8.83h， 生成 (3S,4S)-1-(tert-butoxycarbonyl)-3-hydroxymethyl-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：

  (4S,1'S)-4-hydroxymethyl-1-(1'-phenylethyl)pyrrolidin-2-one 在 六甲基磷酰三胺 、 正丁基锂 、 三苯基甲烷 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.33h， 生成 (3S,4S,1'S)-4-benzyloxymethyl-3-(2''-methylprop-1''-yl)-1-(1'-phenylethyl)pyrrolidin-2-one
  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