(R)-4-tert-butylpyrrolidin-2-one

• 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: (R)-4-tert-butylpyrrolidin-2-one
• 英文别名: (4R)-4-tert-butylpyrrolidin-2-one
• 化学式: C₈H₁₅NO
• 分子量: 141.213
• InChiKey: OFWOAFJRYDAAGI-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3,3-二甲基丁醛 在 镍 氢气 、 magnesium monoperoxyphthalate hexahydrate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 phosphate buffer 、 正己烷 为溶剂， -100.0~70.0 ℃ 、2.0 MPa 条件下， 反应 17.0h， 生成 (R)-4-tert-butylpyrrolidin-2-one
  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

• Co-catalyzed reductive cyclization of azido and cyano substituted α,β-unsaturated esters with NaBH4: enantioselective synthesis of (R)-baclofen and (R)-rolipram
  作者：Abhimanyu S. Paraskar、Arumugam Sudalai

  DOI：10.1016/j.tet.2006.03.017

  日期：2006.5

  Sodium borohydride in combination with a catalytic amount of CoCl2 has been found to be an excellent catalytic system in reductive cyclizations of suitably substituted azido and cyano groups of α,β-unsaturated esters to afford γ and δ-lactams in high yields. The process has been demonstrated for the enantioselective synthesis of (R)-baclofen, (R)-rolipram, and (R)-4-fluorophenylpiperidinone, a key

  已经发现，将硼氢化钠与催化量的CoCl 2结合使用，是对α，β-不饱和酯的适当取代的叠氮基和氰基进行还原环化以提供高收率的γ和δ-内酰胺的优良催化体系。已经证明该方法可用于（R）-baclofen，（R）-咯利普兰和（R）-4-氟苯基哌啶酮（（-）-帕罗西汀的关键中间体）的对映选择性合成。
• US7160907B2
  申请人：——

  公开号：US7160907B2

  公开（公告）日：2007-01-09
• 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.