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
• Article Data: 63

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

Description

N-Boc-piperidine-3-methanol, also known as (+/-)-1-Boc-3-(hydroxymethyl)piperidine, is a white solid with significant applications in the pharmaceutical industry. It is a versatile chemical intermediate used in the synthesis of various biologically active compounds.

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 
• 857298-85-2 N-[(3S)-piperidin-3-ylmethyl]-2-(N-methyl-N-phenylamino)thiazole-4-carboxamide 

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.

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.

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.