116574-71-1

Basic information

• Product Name: N-Boc-piperidine-3-methanol
• Synonyms: (+/-)-BOC-3-PIPERIDINE METHANOL;N-(TERT-BUTOXYCARBONYL)-3-PIPERIDINEMETHANOL;N-BOC-(3S)-PIP(3-CH2OH);N-BOC-3-HYDROXYMETHYLPIPERIDINE;(+/-)-N-BOC-3-PIPERIDINE METHANOL;N-BOC-3-PIPERIDINYL-METHANOL;N-Boc-piperidine-3-methanol;TERT-BUTYL 3-(HYDROXYMETHYL)TETRAHYDRO-1(2H)-PYRIDINECARBOXYLATE
• CAS NO: 116574-71-1
• Molecular Formula: C₁₁H₂₁NO₃
• Molecular Weight: 215.29
• EINECS: 1308068-626-2
• Product Categories: pharmacetical;Piperidine;Heterocyclic Compounds;Building Blocks;C11;Chemical Synthesis;Heterocyclic Building Blocks;Piperidines
• Mol File: 116574-71-1.mol

Chemical Properties

• Melting Point: 77-81°C
• Boiling Point: 308 ºC at 760 mmHg
• Flash Point: 140.1 ºC
• Appearance: Off-white solid
• Density: 1.059 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.479
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: Soluble in methanol and dimethylformamide(DMF).
• PKA: 14.93±0.10(Predicted)
• CAS DataBase Reference: N-Boc-piperidine-3-methanol(CAS DataBase Reference)
• NIST Chemistry Reference: N-Boc-piperidine-3-methanol(116574-71-1)
• EPA Substance Registry System: N-Boc-piperidine-3-methanol(116574-71-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 116574-71-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
N-Boc-piperidine-3-methanol is used as a reactant for the synthesis of several pharmaceutical compounds, including:
1. Pim-1 inhibitors: These are used to target and inhibit the Pim-1 protein, which is involved in cell survival and proliferation, and is often overexpressed in various cancers.
2. Vasopressin1b receptor antagonists: These compounds are used to block the vasopressin1b receptor, which can help in the treatment of conditions like heart failure and hyponatremia.
3. CXCR4 antagonists as anti-HIV agents: These antagonists target the CXCR4 receptor, which is used by HIV to enter human cells, thus potentially providing a therapeutic approach to combat the virus.
4. Amide CCR5 antagonist: N-Boc-piperidine-3-methanol targets the CCR5 receptor, which is another co-receptor used by HIV for cell entry, and can be used in the development of anti-HIV drugs.
5. PSSRI-based inhibitors of S. aureus multidrug efflux pumps: These inhibitors target multidrug efflux pumps in Staphylococcus aureus, which are responsible for antibiotic resistance, potentially leading to more effective treatments for bacterial infections.
6. Human GnRH receptor antagonists: These antagonists block the GnRH receptor, which can be used in the treatment of conditions like endometriosis, prostate cancer, and certain reproductive disorders.

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

Upstream product

• 4606-65-9 3-(hydroxymethy)piperidine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 148672-74-6 ethyl N-(t-butyloxycarbonyl)nipecotate 
• 71962-74-8 Ethyl nipecotate 
• 309735-44-2 3-phenylaminomethyl-piperidine-1-carboxylic acid tert-butyl ester 
• 68-22-4 norethisterone 
• 121-44-8 triethylamine 
• 148763-41-1 1-(tert-butyl) 3-methyl piperidine-1,3-dicarboxylate 
• 71381-75-4 N-(tert-butyloxycarbonyl)nipecotic acid 
• 850761-36-3 tert-butyl 3-iodo-1-piperidinecarboxylate 
• 50-00-0 formaldehyd 
• 140645-20-1 t-butyl (R,S)-3-<(butyryloxy)methyl>-1-piperidine-carboxylate 
• 140695-98-3 (R)-3-Butyryloxymethyl-piperidine-1-carboxylic acid tert-butyl ester 
• 37675-20-0 (R)-3-hydroxymethyl piperidine 

Downstream Products

• 116574-71-1 tert-butyl (3R)-3-(hydroxymethyl)piperidine-1-carboxylate 
• 253177-03-6 3-iodomethylpiperidine-1-carboxylic acid tert-butyl ester 
• 118156-93-7 3-formylpiperidine-1-carboxylic acid tert-butyl ester 
• 162166-99-6 3-methanesulfonyloxymethyl-piperidine-1-carboxylic acid tert-butyl ester 
• 191092-05-4 1-t-butoxycarbonyl-3-(p-toluenesulfonyloxymethyl)piperidine 
• 384830-08-4 tert-butyl (3R)-3-(iodomethyl) piperidine-1-carboxylate 
• 191092-07-6 (R)-tert-butyl 3-((tosyloxy)methyl)piperidine-1-carboxylate 
• 140695-84-7 tert-butyl (3S)-3-(hydroxymethyl)piperidine-1-carboxylate 
• 144448-01-1 (S)-N-tert-butoxycarbonylpiperidin-3-ylmethyl acetate 
• 896053-81-9 4-Benzyl-1-piperidin-3-ylmethyl-piperidine 
• 276872-84-5 3-[4-(4-fluoro-benzyl)-piperidin-1-ylmethyl]-piperidine-1-carboxylic acid tert-butyl ester 
• 189339-80-8 2-chlorobenzenesulfonic acid 3-[(piperidin-3-yl)methoxy]-5-methylphenyl ester 
• 1026901-58-5 1-acetyl-3-{2-[4-(3-methoxyphenyl)butyl]phenoxymethyl}piperidine 
• 189339-76-2 2-Chlorobenzenesulfonic acid 3-[[N-(tert-butoxycarbonyl)piperidin-3-yl]methoxy]-5-methylphenyl ester 

Relevant articles and documents

Synthesis of substituted 1H-imidazol-1-ylmethylpiperidines. Facile separation of 1,4- and 1,5-disubstituted imidazoles

The synthesis of several 1H-imidazol-1-ylmethylpiperidines is described. A method for the regioselective isolation of 1,4-disubstituted imidazoles utilizing the selective quaternization of the 1,5-disubstituted regioisomer was developed.

Exploring Basic Tail Modifications of Coumarin-Based Dual Acetylcholinesterase-Monoamine Oxidase B Inhibitors: Identification of Water-Soluble, Brain-Permeant Neuroprotective Multitarget Agents

Aiming at modulating two key enzymatic targets for Alzheimer's disease (AD), i.e., acetylcholinesterase (AChE) and monoamine oxidase B (MAO B), a series of multitarget ligands was properly designed by linking the 3,4-dimethylcoumarin scaffold to 1,3- and 1,4-substituted piperidine moieties, thus modulating the basicity to improve the hydrophilic/lipophilic balance. After in vitro enzymatic inhibition assays, multipotent inhibitors showing potencies in the nanomolar and in the low micromolar range for hMAO B and eeAChE, respectively, were prioritized and evaluated in human SH-SY5Y cell-based models for their cytotoxicity and neuroprotective effect against oxidative toxins (H2O2, rotenone, and oligomycin-A). The present study led to the identification of a promising multitarget hit compound (5b) exhibiting high hMAO B inhibitory activity (IC50 = 30 nM) and good MAO B/A selectivity (selectivity index, SI = 94) along with a micromolar eeAChE inhibition (IC50 = 1.03 μM). Moreover, 5b behaves as a water-soluble, brain-permeant neuroprotective agent against oxidative insults without interacting with P-gp efflux system.

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.

NOVEL HISTONE METHYLTRANSFERASE INHIBITORS

The present invention relates to novel compounds of formula (I) as defined herein. The compounds are inhibitors of histone methyltransferases of the seven-beta-strand family, in particular of KMT9.

Radical hydroxymethylation of alkyl iodides using formaldehyde as a C1 synthon

Radical hydroxymethylation using formaldehyde as a C1 synthon is challenging due to the reversible and endothermic nature of the addition process. Here we report a strategy that couples alkyl iodide building blocks with formaldehyde through the use of photocatalysis and a phosphine additive. Halogen-atom transfer (XAT) from α-aminoalkyl radicals is leveraged to convert the iodide into the corresponding open-shell species, while its following addition to formaldehyde is rendered irreversible by trapping the transient O-radical with PPh3. This event delivers a phosphoranyl radical that re-generates the alkyl radical and provides the hydroxymethylated product.

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.

JANUS KINASE 1 SELECTIVE INHIBITOR AND PHARMACEUTICAL USE THEREOF

Janus kinase 1 selective inhibitors and pharmaceutical use thereof are provided.