1,1-Dimethylethyl 3-[(acetyloxy)methyl]-1-piperidinecarboxylate | 355375-63-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1,1-Dimethylethyl 3-[(acetyloxy)methyl]-1-piperidinecarboxylate
• 英文别名: tert-butyl 3-(acetyloxymethyl)piperidine-1-carboxylate
• CAS: 355375-63-2
• 化学式: C₁₃H₂₃NO₄
• mdl: MFCD24393717
• 分子量: 257.33
• InChiKey: DSKBLSVOGMOGAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.846
• 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：

  1,1-Dimethylethyl 3-[(acetyloxy)methyl]-1-piperidinecarboxylate 在 protease type XVIII from fungal Rhizopus sp. 作用下， 以 aq. phosphate buffer 为溶剂， 以88.9%的产率得到
  参考文献：
  名称：

  Chemical and Enzymatic Resolution of (R,S)-N-(tert-Butoxycarbonyl)-3-hydroxymethylpiperidine

  摘要：

  (S)-N-(tert-Butoxycarbonyl)-3-hydroxymethylpiperidine 1 was made from (R,S)-3-hydroxymethylpiperidine 2 via fractional crystallization of the corresponding L(-)-dibenzoyl tartarate salt 3 followed by hydrolysis and acylation. Lipase from Pseudomonas cepacia was found to be the best enzyme for the stereospecific resolution of (RS)-N-(tert-butoxycarbonyl)-3-hydroxymethylpiperidine 4. (S)-N-(tert-Butoxycarbonyl)-3-hydroxymethylpiperidine I was obtained in 16% yield and >95% enantiomeric excess (ee) by hydrolysis of (R,S)-acetate 5 by lipase PS from Pseudomonas cepacia. Lipase PS-catalyzed esterification of the (RS)-N-(tert-butoxycarbonyl)-3-hydroxymethylpiperidine 4 with succinic anhydride provided the S-hemisuccinate ester 6, which could be easily separated and hydrolyzed by base to the (S)-N-(tert-butoxycarbonyl)-3-hydroxymethylpiperidine 1. The yield and ee could be improved greatly by repetition of the process. Using the repeated esterification procedure(S)-N-(tert-butoxycarbonyl)-3-hydroxymethylpiperidine I was obtained in 32% yield (maximum theoretical yield 50%) and 98.9% ee.

  DOI：

  10.1021/op010210b