163438-09-3

Basic information

• Product Name: (R)-Boc-Nipecotic acid
• Synonyms: 1-[(2-methylpropan-2-yl)oxycarbonyl]piperidine-3-carboxylic acid;BOC-R-NIP-OH;BOC-D-NIP-OH;D-1-BOC-NIPECOTIC ACID;(R)-1-BOC-NIPECOTIC ACID;(R)-1-BOC-PIPERIDINE-3-CARBOXYLIC ACID;(R)-1-(TERT-BUTOXYCARBONYL)PIPERIDINE-3-CARBOXYLIC ACID;(R)-BOC-NIP
• CAS NO: 163438-09-3
• Molecular Formula: C₁₁H₁₉NO₄
• Molecular Weight: 229.27
• Product Categories: chiral;Chiral Reagent;Piperidines;piperidine
• Mol File: 163438-09-3.mol

Chemical Properties

• Boiling Point: 353.2 °C at 760 mmHg
• Flash Point: 167.4 °C
• Appearance: White/Crystalline Powder
• Density: 1.164 g/cm³
• Vapor Pressure: 6.15E-06mmHg at 25°C
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 4.49±0.20(Predicted)
• BRN: 5539297
• CAS DataBase Reference: (R)-Boc-Nipecotic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-Boc-Nipecotic acid(163438-09-3)
• EPA Substance Registry System: (R)-Boc-Nipecotic acid(163438-09-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 163438-09-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(R)-Boc-Nipecotic acid is used as an organic chemical synthesis intermediate for the development of pharmaceutical compounds. Its unique structure allows for the creation of new molecules with potential therapeutic applications, contributing to the advancement of drug discovery and development.
Used in Chemical Research:
In the field of chemical research, (R)-Boc-Nipecotic acid serves as a crucial building block for the synthesis of complex organic molecules. Its versatility in chemical reactions enables researchers to explore new pathways and create novel compounds with diverse applications.
Used in Material Science:
(R)-Boc-Nipecotic acid can also be utilized in the development of new materials with specific properties. Its integration into the synthesis process can lead to the creation of materials with enhanced characteristics, such as improved stability or reactivity, which can be applied in various industries.

InChI:InChI=1/C11H19NO4/c1-11(2,3)16-10(15)12-6-4-5-8(7-12)9(13)14/h8H,4-7H2,1-3H3,(H,13,14)/p-1/t8-/m1/s1

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 498-95-3 (R)-nipecotic acid 
• 194726-40-4 (3R)-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester 
• 498-95-3 nipecotic acid 
• 300-08-3 arecoline hydrobromide 
• 92600-27-6 1-(1-chloroethyl) 3-methyl 5,6-dihydropyridine-1,3(2H)-dicarboxylate 
• 86447-11-2 1-tert-butoxycarbonyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid 
• 6027-92-5 guvacine hydrobromide 
• 495-19-2 norarecoline 

Downstream Products

• 457895-04-4 (R)-3-{2-[(R)-1-(4-Chloro-benzyl)-2-(4-cyclohexyl-4-[1,2,4]triazol-1-ylmethyl-piperidin-1-yl)-2-oxo-ethylcarbamoyl]-ethylcarbamoyl}-piperidine-1-carboxylic acid tert-butyl ester 
• 798576-71-3 N-(tert-butyloxycarbonyl)piperidine-3(R)-carboxylic acid [2-(3,4-dibenzyloxy-5-oxo-2,5-dihydrofuran-2(R)-yl)-2(S)-hydroxyethyl] ester 
• 884510-86-5 (R)-tert-butyl 3-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate 
• 915226-43-6 (R)-tert-butyl 3-carbamoylpiperidine-1-carboxylate 
• 215610-19-8 ((1S,2S)-2-Benzyl-3-{(R)-3-[(S)-3-((1R,2S)-1-ethyl-2-methylcarbamoyl-propylcarbamoyl)-piperidine-1-carbonyl]-piperidin-1-yl}-3-oxo-1-phenylsulfanylmethyl-propyl)-carbamic acid tert-butyl ester 
• 1026290-16-3 (S)-5-Phenyl-3-[((R)-piperidine-3-carbonyl)-amino]-pent-4-ynoic acid methyl ester 

Relevant articles and documents

OXA-SPIRODIPHOSPHINE LIGAND AND METHOD FOR ASYMMETRIC HYDROGENATION OF alpha, beta-UNSATURATED CARBOXYLIC ACIDS

The present invention provides an oxa-spirodiphosphine ligand having a structure of general Formula (I) below: wherein in general Formula (I), R1, R2, R3 and R4 are the same, and are alkyl, alkoxy, aryl, aryloxy

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.

Piperidine scaffold as the novel P2-ligands in cyclopropyl-containing HIV-1 protease inhibitors: Structure-based design, synthesis, biological evaluation and docking study

A series of potent HIV-1 protease inhibitors, containing diverse piperidine analogues as the P2-ligands, 4-substituted phenylsulfonamides as the P2'-ligands and a hydrophobic cyclopropyl group as the P1'-ligand, were designed, synthesized and evaluated in this work. Among these twenty-four target compounds, many of them exhibited excellent activity against HIV-1 protease with half maximal inhibitory concentration (IC50) values below 20 nM. Particularly, compound 22a containing a (R)-piperidine-3-carboxamide as the P2-ligand and a 4-methoxylphenylsulfonamide as the P2'-ligand exhibited the most effective inhibitory activity with an IC50 value of 3.61 nM. More importantly, 22a exhibited activity with inhibition of 42% and 26% against wild-type and Darunavir (DRV)-resistant HIV-1 variants, respectively. Additionally, the molecular docking of 22a with HIV-1 protease provided insight into the ligand-binding properties, which was of great value for further study.

Oxa-spiral diphosphine ligand and application thereof in alpha, beta-unsaturated carboxylic acid asymmetric hydrogenation

The invention provides an oxa-spiral diphosphine ligand. The oxa-spiral diphosphine ligand has a structure shown by a general formula (I) as shown in description, wherein R1, R2, R3 and R4 in the general formula (I) are same and are alkyl, alkoxy, aryl, aroxyl, or hydrogen atoms; R1, R2, R3 and R4 comprise forms of ring formation, non-ring formation, any two ring formation or multiple-ring formation between pairs; R5 and R6 are alkyl, aryl or hydrogen atoms; and R7 and R8 are alkyl or benzyl or aryl. The invention further provides application of the oxa-spiral diphosphine ligand O-SDP in the alpha, beta-unsaturated carboxylic acid asymmetric hydrogenation. A complex of the oxa-spiral diphosphine ligand O-SDP and ruthenium has excellent activity and enantioselectivity in the asymmetric hydrogenation of the alpha, beta-unsaturated carboxylic acid in multiple types, and a chiral carboxylic acid product is obtained with the enantioselectivity being up to 99%. The synthesis method can be applied to the construction of a core skeleton of chemical molecules with important activity, wherein the chemical molecules comprise Paroxetine, Femoxetine, nipecotic acid and Sacubitril.

MORPHINAN DERIVATIVE

A compound represented by the following general formula (I), wherein R1 represents hydrogen, C1-10 alkyl, cycloalkylalkyl where the cycloalkyl moiety has 3 to 6 carbon atoms and the alkylene moiety has 1 to 5 carbon atoms, or the like, R2 represents a 4- to 7-membered saturated heterocycle containing one or two heteroatoms which may be the same or different and are selected from N, O, and S, and two or more carbon atoms as ring-constituting atoms, the heterocycle may be substituted with a substituent such as an oxo group, R2 binds to Y via a carbon atom as a ring-constituting atom of R2, R3, R4, and R5, which are the same or different, represent hydrogen; hydroxy; or the like, R6a and R6b, which are the same or different, represent hydrogen or the like, R7 and R8, which are the same or different, represent hydrogen or the like, R9 and R10, which are the same or different, represent hydrogen or the like, X represents O or CH2, and Y represents C(= O) or the like), a tautomer of the compound, a stereoisomer of the compound, a pharmaceutically acceptable salt thereof, or a solvate thereof is used as an anxiolytic, an antidepressant, or the like.

Iridium-catalyzed enantioselective hydrogenation of unsaturated heterocyclic acids

Spiral binding: A highly enantioselective hydrogenation of unsaturated heterocyclic acids has been developed by using chiral iridium/spirophosphino oxazoline catalysts (see scheme; BArF-=tetrakis[3,5- bis(trifluoromethyl)phenyl]borate, Boc=tert-butoxycarbonyl). This reaction provided an efficient method for the preparation of optically active heterocyclic acids with excellent enantioselectivities. Copyright

Synthesis and evaluation of new polyenic compounds as potential PPARs modulators

In order to identify new leads for the treatment of type 2 diabetes, polyenic molecules A and B derived from nipecotic acid and dienol derivatives C have been prepared and their effect on PPARs transcriptional activity evaluated and compared to that of rosiglitazone, WY14,643 and GW501516. Among the synthesized compounds, dienol 39 is the most active, increasing WY14,643 PPARα response and demonstrating partial agonist properties on rosiglitazone PPARγ.

Structure-based design of pseudopeptidic inhibitors for SIRT1 and SIRT2

The lack of substrate-bound crystal structures of SIRT1 and SIRT2 complicates the drug design for these targets. In this work, we aim to study whether SIRT3 could serve as a target structure in the design of substrate based pseudopeptidic inhibitors of SIRT1 and SIRT2. We created a binding hypothesis for pseudopeptidic inhibitors, synthesized a series of inhibitors, and studied how well the fulfillment of the binding criteria proposed by the hypothesis correlated with the in vitro inhibitory activities. The chosen approach was further validated by studying docking results between 12 different SIRT3, Sir2Tm, SIRT1 and SIRT2 X-ray structures and homology models in different conformational forms. It was concluded that the created binding hypothesis can be used in the design of the substrate based inhibitors of SIRT1 and SIRT2 although there are some reservations, and it is better to use the substrate-bound structure of SIRT3 instead of the available apo-SIRT2 as the target structure.

TREATMENT OF METABOLIC SYNDROME WITH CYCLIC AMIDES

The present application relates to a compound of formula (I) or a pharmaceutically acceptable salt thereof, wherein the variables are'as defined in the claims. The present application also relates to the treatment of metabolic syndrome or disorders associated with metabolic syndrome in an affected mammal by administering a compound of formula (I) or a pharmaceutically acceptable salt thereof.

Novel non-peptide nociceptin/orphanin FQ receptor agonist, 1-[1-(1-Methylcyclooctyl)-4-piperidinyl]-2-[(3R)-3-piperidinyl] -1H-benzimidazole: Design, synthesis, and structure-activity relationship of oral receptor occupancy in the brain for orally potent

An endogenous heptadecapeptide, nociceptin/orphanin FQ (N/OFQ), and a G-protein-coupled receptor, N/OFQ peptide (NOP) receptor [or opioid-receptor-like-1 (ORL1) receptor], have been described in terms of its structure, distribution, and pharmacology. Thus