Application of the PMC protecting group in the efficient synthesis of 4,4-disubstituted piperidines

Ralbovsky JL; Lisko JG; He W

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Application of the PMC protecting group in the efficient synthesis of 4,4-disubstituted piperidines

机译：PMC保护基在有效合成4,4-二取代哌啶中的应用

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An efficient synthesis of the 4,4-disubstituted piperidine scaffold 1 was accomplished by treating the PMC N-protected alpha,beta-unsaturated ethyl cyanoacetate 9 with various Grignard reagents (R1MgX). Subsequent heating at 190 degrees C in a strong base provided carboxylic acids 12-20b in good yield. The PMC group was easily removed at room temperature with 33% HBr in acetic acid.

机译：通过用各种格氏试剂（R1MgX）处理PMC N保护的α，β-不饱和氰基乙酸乙酯9，可以完成4,4-二取代哌啶骨架1的有效合成。随后在强碱中于190℃加热，以良好的产率提供了羧酸12-20b。在室温下，用33％HBr的乙酸溶液很容易除去PMC基团。

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《Synthetic Communications》 |2005年第12期|共13页
作者
Ralbovsky JL; Lisko JG; He W;
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正文语种 eng
中图分类有机化学;
关键词
1; 4-addition; 4; 4-disubstituted piperidines; PMC protecting group;

机译：1;4-加成;4;4-二取代哌啶;PMC保护基;

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1. Application of the PMC protecting group in the efficient synthesis of 4,4-disubstituted piperidines [J] . Ralbovsky JL, Lisko JG, He W Synthetic Communications . 2005,第12期

机译：PMC保护基在有效合成4,4-二取代哌啶中的应用
2. Synthesis and receptor binding studies of novel 4,4-disubstituted arylalkyl/arylalkylsulfonyl piperazine and piperidine-based derivatives as a new class of σ1 ligands [J] . SadeghzadehM., SheibaniS., GhandiM., European Journal of Medicinal Chemistry: Chimie Therapeutique . 2013,第Null期

机译：新型4,4-二取代芳烷基/芳烷基磺酰基哌嗪和哌啶基衍生物作为新型σ1配体的合成及受体结合研究
3. Effects of Extended Aryl-Substituted Bisoxazoline Ligands in Asymmetric Synthesis - Efficient Synthesis and Application of 4,4'-Bis(l-Naphthyl)-,4,4'-Bis(2-Naphthyl)-and 4,4'-Bis(9-Anthryl)-2,2'-isopropylidenebis(l,3-oxazolines) [J] . Floris L.van Delft, Roy P.M.Storcken, Koen F.W.Hekking, European journal of organic chemistry . 2005,第23期

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4. PROTECTING-GROUP-FREE SYNTHESIS OF PIPERIDINE AZASUGARS [C] . Corkran H. M., Dangerfield E. M., Munneke S. International Carbohydrate Symposium . 2013

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5. Synthesis and characterization of novel platinum(II) and platinum(IV) complexes containing 4,4'-disubstituted-2,2'- bipyridine ligands for the treatment of cancer. [D] . Vo, Van. 2014

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6. Application of new catalytic phosphate protecting groups for the highly efficient phosphotriester oligonucleotide synthesis. [O] . V A Efimov, A A Buryakova, I Y Dubey, 1986

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7. Synthesis of atropisomeric 2,2'-disubstituted-3,3'-quinazolin-4,4'-diones and their application in asymmetric synthesis [O] . Pertusati Fabrizio 2007

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Application of the PMC protecting group in the efficient synthesis of 4,4-disubstituted piperidines

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