(3R,4R)-3-benzyloxymethyl-1-(tert-butoxycarbonyl)-4-(2'-methylprop-1'-yl)pyrrolidine | 641634-66-4

• 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: (3R,4R)-3-benzyloxymethyl-1-(tert-butoxycarbonyl)-4-(2'-methylprop-1'-yl)pyrrolidine
• 英文别名: tert-butyl (3R,4R)-3-(2-methylpropyl)-4-(phenylmethoxymethyl)pyrrolidine-1-carboxylate
• CAS: 641634-66-4
• 化学式: C₂₁H₃₃NO₃
• 分子量: 347.498
• InChiKey: BLLHKTJYBGNLNN-RBUKOAKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,4R)-3-benzyloxymethyl-1-(tert-butoxycarbonyl)-4-(2'-methylprop-1'-yl)pyrrolidine 在 palladium on activated charcoal 盐酸 、 甲酸 、 jones' reagent 、 Amberlite IRA 900 作用下， 以 乙醇 、 环己烷 、 水 、 丙酮 为溶剂， 反应 26.58h， 生成 (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 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 氯甲酸氯乙酯 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 7.83h， 生成 (3R,4R)-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