methyl (3R,4R)-1-(tert-butoxycarbonyl)-4-(2'-methylprop-1'-yl)-3-pyrrolidinecarboxylate | 641634-68-6

• 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: methyl (3R,4R)-1-(tert-butoxycarbonyl)-4-(2'-methylprop-1'-yl)-3-pyrrolidinecarboxylate
• 英文别名: 1-O-tert-butyl 3-O-methyl (3R,4R)-4-(2-methylpropyl)pyrrolidine-1,3-dicarboxylate
• CAS: 641634-68-6
• 化学式: C₁₅H₂₇NO₄
• 分子量: 285.384
• InChiKey: NYJSASXBMYXNFJ-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (3R,4R)-1-(tert-butoxycarbonyl)-4-(2'-methylprop-1'-yl)-3-pyrrolidinecarboxylate 在 盐酸 作用下， 以 水 为溶剂， 反应 24.0h， 以72%的产率得到(3R,4R)-4-(2'-methylprop-1'-yl)-3-pyrrolidine carboxylic acid hydrochloride
  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：

  (3R,4R,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 、 jones' reagent 、 Amberlite IRA 900 、 氯甲酸氯乙酯 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 环己烷 、 丙酮 为溶剂， 反应 10.41h， 生成 methyl (3R,4R)-1-(tert-butoxycarbonyl)-4-(2'-methylprop-1'-yl)-3-pyrrolidinecarboxylate
  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