(S)-methyl 3-(4-chlorophenyl)-4-[(R)-2-methoxymethylpyrrolidin-1-ylimino]butanoate

• 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: (S)-methyl 3-(4-chlorophenyl)-4-[(R)-2-methoxymethylpyrrolidin-1-ylimino]butanoate
• 英文别名: methyl (3R,4E)-3-(4-chlorophenyl)-4-[(2S)-2-(methoxymethyl)pyrrolidin-1-yl]iminobutanoate
• 化学式: C₁₇H₂₃ClN₂O₃
• 分子量: 338.834
• InChiKey: LSQHOWCKCSGMBO-ABOJNYCISA-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：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  51.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-methyl 3-(4-chlorophenyl)-4-[(R)-2-methoxymethylpyrrolidin-1-ylimino]butanoate 在 盐酸 、 magnesium monoperoxyphthalate hexahydrate 作用下， 以 甲醇 、 phosphate buffer 为溶剂， 反应 17.5h， 生成 R(+)-巴氯芬盐酸盐
  参考文献：
  名称：

  Asymmetric Synthesis of β-Substituted γ-Lactams Employing the SAMP-/RAMP-Hydrazone Methodology. Application to the Synthesis of (R)-(-)-Baclofen

  摘要：

  A short and efficient asymmetric synthesis of beta-substituted gamma-lactams is described. Key steps are the alpha-alkylation of aldehyde SAMP-hydrazones with alkyl bromoacetates, their MMPP mediated conversion to the corresponding nitriles and a reductive cyclization with Raney Ni or Ni boride to the title pyrrolidin-2-ones. The P-substituted gamma-lactams are obtained in three steps, good overall yields (27-78%) and excellent enantiomeric excesses (ee = 93-99%). The applicability of this procedure for the asymmetric synthesis of GABAs (gamma-aminobutyric acids) is demonstrated for (R)-(-)-baclofen hydrochloride, which is obtained in 4 steps, 55% yield and 94% ee.

  DOI：

  10.3987/com-05-s(k)41
• 作为产物：
  描述：

  (4-氯苯基)乙醛 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 生成 (S)-methyl 3-(4-chlorophenyl)-4-[(R)-2-methoxymethylpyrrolidin-1-ylimino]butanoate
  参考文献：
  名称：

  Asymmetric Synthesis of β-Substituted γ-Lactams Employing the SAMP-/RAMP-Hydrazone Methodology. Application to the Synthesis of (R)-(-)-Baclofen

  摘要：

  A short and efficient asymmetric synthesis of beta-substituted gamma-lactams is described. Key steps are the alpha-alkylation of aldehyde SAMP-hydrazones with alkyl bromoacetates, their MMPP mediated conversion to the corresponding nitriles and a reductive cyclization with Raney Ni or Ni boride to the title pyrrolidin-2-ones. The P-substituted gamma-lactams are obtained in three steps, good overall yields (27-78%) and excellent enantiomeric excesses (ee = 93-99%). The applicability of this procedure for the asymmetric synthesis of GABAs (gamma-aminobutyric acids) is demonstrated for (R)-(-)-baclofen hydrochloride, which is obtained in 4 steps, 55% yield and 94% ee.

  DOI：

  10.3987/com-05-s(k)41

文献信息

• Asymmetric Synthesis of β-Substituted γ-Lactams Employing the SAMP-/RAMP-Hydrazone Methodology. Application to the Synthesis of (R)-(-)-Baclofen
  作者：Dieter Enders、Oliver Niemeier

  DOI：10.3987/com-05-s(k)41

  日期：——

  A short and efficient asymmetric synthesis of beta-substituted gamma-lactams is described. Key steps are the alpha-alkylation of aldehyde SAMP-hydrazones with alkyl bromoacetates, their MMPP mediated conversion to the corresponding nitriles and a reductive cyclization with Raney Ni or Ni boride to the title pyrrolidin-2-ones. The P-substituted gamma-lactams are obtained in three steps, good overall yields (27-78%) and excellent enantiomeric excesses (ee = 93-99%). The applicability of this procedure for the asymmetric synthesis of GABAs (gamma-aminobutyric acids) is demonstrated for (R)-(-)-baclofen hydrochloride, which is obtained in 4 steps, 55% yield and 94% ee.