140695-84-7

Usage

Uses

Used in Pharmaceutical Industry:
(S)-1-Boc-3-(hydroxymethyl)piperidine is used as a pharmaceutical intermediate for the development of new drugs and therapeutic agents. Its unique structure and reactivity make it a valuable component in the synthesis of various pharmaceutical compounds, particularly those targeting the central nervous system and other biological processes.
As a pharmaceutical intermediate, (S)-1-Boc-3-(hydroxymethyl)piperidine plays a critical role in the synthesis of a wide range of medications, including those used to treat neurological disorders, pain management, and other medical conditions. Its versatility and specificity in chemical reactions contribute to the development of more effective and targeted treatments in the pharmaceutical industry.

InChI:InChI=1/C11H21NO3/c1-11(2,3)15-10(14)12-6-4-5-9(7-12)8-13/h9,13H,4-8H2,1-3H3/t9-/m1/s1

Upstream product

• 108-05-4 vinyl acetate 
• 116574-71-1 (±)-tert-butyl 3-(hydroxymethyl)piperidine-1-carboxylate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 4606-65-9 (S)-(hydroxymethyl)piperidine 
• 136866-84-7 (S)-piperidin-3-ylmethyl acetate 
• 191599-51-6 ethyl (S)-1-[(tert-butoxy)carbonyl]piperidine-3-carboxylate 
• 163343-71-3 (S)-ethyl nipecotate (S,S)-hydrogen tartrate 
• 1255150-67-4 C₁₇H₃₅NO₃Si 
• 37675-20-0 (R)-3-hydroxymethyl piperidine 
• 140645-20-1 t-butyl (R,S)-3-<(butyryloxy)methyl>-1-piperidine-carboxylate 
• 4606-65-9 3-(hydroxymethy)piperidine 
• 108-30-5 succinic acid anhydride 
• 88495-54-9 (3S)-1-(tert-butoxycarbonyl)piperidine-3-carboxylic acid 
• 206554-24-7 (S)-3-Acetoxymethyl-piperidine-1-carboxylic acid benzyl ester 

Downstream Products

• 384830-08-4 tert-butyl (3R)-3-(iodomethyl) piperidine-1-carboxylate 
• 191092-07-6 (R)-tert-butyl 3-((tosyloxy)methyl)piperidine-1-carboxylate 
• 857298-85-2 N-[(3S)-piperidin-3-ylmethyl]-2-(N-methyl-N-phenylamino)thiazole-4-carboxamide 
• 364356-36-5 3-({[2-(methyl-phenyl-amino)-thiazole-4-carbonyl]-amino}-methyl)-piperidine-1-carboxylic acid tert-butyl ester 

Relevant academic research and scientific papers

An efficient synthesis of 3(S)-aminopiperidine-5(R)-carboxylic acid as a cyclic β,γ′-diamino acid

An orthogonally protected β,γ′-diamino acid 6 possessing conformationally-constrained ring system was synthesized as a novel cyclic amino acid analogue. This synthesis involves as key steps chemoselective enzymatic hydrolysis of cis-piperidine-3,5-dicarboxylic ester derivative followed by efficient kinetic resolution of the partially resolved half-acid to afford the C1-symmetric piperidine-3,5-dicarboxylic acid monoester in high enantiomeric excess (>98% ee). The optically active half-acid was transformed to the cyclic amino acid via Curtius-type rearrangement.

Design and evaluation of novel piperidine HIV-1 protease inhibitors with potency against DRV-resistant variants

A novel class of HIV-1 protease inhibitors with flexible piperidine as the P2 ligand was designed with the aim of improving extensive interactions with the active subsites. Many inhibitors exhibited good to excellent inhibitory effect on enzymatic activity and viral infectivity. In particular, inhibitor 3a with (R)-piperidine-3-carboxamide as the P2 ligand and 4-methoxybenzenesulfonamide as the P2’ ligand showed an enzyme Ki value of 29 pM and antiviral IC50 value of 0.13 nM, more than six-fold enhancement of activity compared to DRV. Furthermore, there was no significant change in potency against DRV-resistant mutations and HIV-1NL4?3 variant for 3a. Besides, inhibitor 3a exhibited potent antiviral activity against subtype C variants with low nanomole EC50 values. In addition, the molecular modeling revealed important hydrogen bonds and other favorable van der Waals interactions with the backbone atoms of the protease and provided insight for designing and optimizing more potent HIV-1 protease inhibitors.

Discovery of 3-amino-4-{(3S)-3-[(2-ethoxyethoxy)methyl]piperidin-1-yl}thieno[2,3-b]pyridine-2-carboxamide (DS96432529): A potent and orally active bone anabolic agent

The continuing investigation of SAR of 3-aminothieno[2,3-b]pyridine-2-carboxamide derivatives has been described. In this study, C4-piperidine derivatives with polar functional groups were synthesized to develop orally available bone anabolic agents. The optimized compound 9o (DS96432529), which exhibited the best PK profile and high in vitro activity, showed the highest in vivo efficacy in this series. Moreover, significant synergistic effects were observed following co-administration of DS96432529 and alendronate or parathyroid hormone. The mechanism of action is most likely mediated through CDK8 inhibition.

SUBSTITUTED (PIPERIDIN-1-YL)ARYL ANALOGUES FOR MODULATING AVILACTIVITY

In one aspect, the disclosure relates to compounds useful to regulate, limit, or inhibit the expression of AVIL (advillin), methods of making same, pharmaceutical compositions comprising same, and methods of treating disorders associated with AVIL dysregulation using same. In aspects, the disclosed compounds, compositions and methods are useful for treating disorders or diseases in which the regulation, limitation, or inhibition of the expression of AVIL can be clinically useful, such as, for example, the treatment of cancer. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present disclosure.

Palladium-catalyzed ring-closing reaction via C-N bond metathesis for rapid construction of saturated N-heterocycles

The ring-closing reactions based on chemical bond metathesis enable the efficient construction of a wide variety of cyclic systems which receive broad interest from medicinal and organic communities. However, the analogous reaction with C-N bond metathesis as a strategic fundamental step remains an unanswered challenge. Herein, we report the design of a new fundamental metallic C-N bond metathesis reaction that enables the palladium-catalyzed ring-closing reaction of aminodienes with aminals. The reactions proceed efficiently under mild conditions and exhibit broad substrate generality and functional group compatibility, leading to a wide variety of 5- to 16-membered N-heterocycles bearing diverse frameworks and functional groups.

Synthetic method for (R)-N-tert-butoxycarbonyl-3-hydroxymethylpiperidine

The invention discloses a synthetic method for (R)-N-tert-butoxycarbonyl-3-hydroxymethylpiperidine. The method comprises the following four steps: synthesizing ethyl 3-piperidinecarboxylate (compoundII), synthesizing ethyl (R)-nipecotate-L-tartarate (compound III), synthesizing ethyl (R)-N-Boc-3-piperidinecarboxylate (compound IV) and synthesizing the (R)-N-tert-butoxycarbonyl-3-hydroxymethylpiperidine (compound V); and the method comprises the following special steps: synthesizing the compound II by using 3-piperidinecarboxylic acid (compound I) as a raw material through chloroacylation andethanol esterification; performing a salt formation reaction to form the compound III; adding a Boc anhydride and performing a reaction to obtain the compound IV; and finally performing sodium borohydride reduction to obtain the compound V. The method provided by the invention has the advantages of mild reaction conditions, environmental friendliness, simple operation steps, better reproducibilityand high practicability, and is suitable for industrial mass production of the (R)-N-tert-butoxycarbonyl-3-hydroxymethylpiperidine.

KRAS G12C INHIBITORS

The present invention relates to compounds that inhibit KRas G12C. In particular, the present invention relates to compounds that irreversibly inhibit the activity of KRas G12C, pharmaceutical compositions comprising the compounds and methods of use therefor.

Novel Triazolopyrazine Derivatives and Use Thereof

The present invention relates to novel triazolopyrazine derivatives or a pharmaceutically acceptable salt, and a pharmaceutical composition for inhibiting c-Met tyrosine kinase activity and a pharmaceutical composition for preventing or treating hyperproliferative disorders, containing the same as active ingredients. The present invention effectively inhibits c-Met tyrosine kinase activity, thereby being able to be useful as a drug for various hyperproliferative disorders such as cancers, psoriasis, rheumatoid arthritis, diabetic retinitis, etc. related to excessive cell proliferation and growth by abnormal kinase activation.

KRAS G12C INHIBITORS

The present invention relates to compounds that inhibit KRas G12C. In particular, the present invention relates to compounds that irreversibly inhibit the activity of KRas G12C, pharmaceutical compositions comprising the compounds and methods of use therefor.

COMPOUNDS USEFUL AS KINASE INHIBITORS

This invention relates to novel compounds. The compounds of the invention are tyrosine kinase inhibitors. Specifically, the compounds of the invention are useful as inhibitors of Bruton's tyrosine kinase (BTK).The invention also contemplates the use of the compounds for treating conditions treatable by the inhibition of Bruton's tyrosine kinase, for example cancer, lymphoma, leukemia and immunological diseases.