124443-68-1

Basic information

• Product Name: N-Boc-Piperidine-4-carboxylic acid methyl ester
• Synonyms: tert-Butyl methyl piperidine-1,4-dicarboxylate;N-Boc-Isonipecotic acid methyl ester;1-(tert-butyl) 4-methyl tetrahydro-1,4(2H)-pyridinedicarboxylate;N-Boc- Piperidine-4-carboxylate;1-Boc-Piperidine-4-carboxylic acid methyl ester;1,4-Piperidinedicarboxylic acid, 1-(1,1-dimethylethyl) 4-methyl ester;Methyl-boc-piperidine-4-carboxylate;Methyl 1-(tert-Butoxycarbonyl)-4-piperidinecarboxylate
• CAS NO: 124443-68-1
• Molecular Formula: C₁₂H₂₁NO₄
• Molecular Weight: 243.3
• Product Categories: pharmacetical;Acids and Derivatives;Amines and Anilines
• Mol File: 124443-68-1.mol

Chemical Properties

• Melting Point: 33.0 to 37.0 °C
• Boiling Point: 307.4 °C at 760 mmHg
• Flash Point: 139.7 °
• Appearance: /
• Density: 1.094 g/cm³
• Vapor Pressure: 3.83E-06mmHg at 25°C
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: soluble in Methanol
• PKA: -2.29±0.40(Predicted)
• CAS DataBase Reference: N-Boc-Piperidine-4-carboxylic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-Boc-Piperidine-4-carboxylic acid methyl ester(124443-68-1)
• EPA Substance Registry System: N-Boc-Piperidine-4-carboxylic acid methyl ester(124443-68-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• HazardClass: IRRITANT
• Hazardous Substances Data: 124443-68-1(Hazardous Substances Data)

Usage

Chemical Properties

White solid

InChI:InChI=1/C12H21NO4/c1-8-5-6-13(9(7-8)10(14)15)11(16)17-12(2,3)4/h8-9H,5-7H2,1-4H3,(H,14,15)/p-1

Upstream product

• 7462-86-4 methyl piperidine-4-carboxylate hydrochloride 
• 1538-75-6 2,2-dimethylpropanoic anhydride 
• 67-56-1 methanol 
• 84358-13-4 N-[(tert-butoxy)carbonyl]piperidine-4-carboxylic acid 
• 498-94-2 isonipecotic acid 
• 24424-99-5 di-tert-butyl dicarbonate 
• 2971-79-1 isonipecotic acid methyl ester 
• 201230-82-2 carbon monoxide 
• 75-65-0 tert-butyl alcohol 
• 301673-14-3 tert-butyl 4-iodopiperidine-1-carboxylate 
• 3236-56-4 dipercarbonate de O,O-t-butyle 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 74-88-4 methyl iodide 

Downstream Products

• 124443-69-2 4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]carbonyl]-1-piperidinecarboxylic acid,1,1-dimethylethyl ester 
• 287202-48-6 4-(4-but-2-ynyloxybenzenesulfonyl)-piperidine-1,4-dicarboxylic acid tert-butyl ester methyl ester 
• 578021-55-3 1-tert-butyl 4-methyl 4-ethylpiperidine-1,4-dicarboxylate 
• 741687-06-9 1-tert-butyl 4-methyl 4-benzylpiperidine-1,4-dicarboxylate 
• 441774-09-0 1-(tert-butyl) 4-methyl 4-allylpiperidine-1,4-dicarboxylate 
• 137076-22-3 tert butyl 4-formylpiperidine-1-carboxylate 
• 724790-59-4 4-methyl-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-methyl ester 
• 177990-44-2 N-t-butoxycarbonyl-4-(2-methylbenzyl)-isonipecotic acid methyl ester 
• 913264-42-3 tert-butyl 4-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidine-1-carboxylate 
• 885500-37-8 4-(4-chlorobenzyl)piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-methyl ester 
• 1006044-27-4 1-tert-butyl 4-methyl 4-(hydroxymethyl)piperidine-1,4-dicarboxylate 
• 1314319-01-1 1-tert-butyl 4-methyl 4-(chloromethyl)piperidine-1,4-dicarboxylate 
• 1312131-45-5 tert-butyl 4-(chloromethyl)-4-(hydroxymethyl)piperidine-1-carboxylate 
• 1314319-14-6 C₂₀H₃₀N₂O₂ 

Relevant articles and documents

Sustainable Route Toward N-Boc Amines: AuCl3/CuI-Catalyzed N-tert-butyloxycarbonylation of Amines at Room Temperature

N-tert-butoxycarbonyl (N-Boc) amines are useful intermediates in synthetic/medicinal chemistry. Traditionally, they are prepared via an indirect phosgene route with poor atom economy. Herein, a step- and atom-economic synthesis of N-Boc amines from amines, t-butanol, and CO was reported at room temperature. Notably, this N-tert-butyloxycarbonylation procedure utilized ready-made substrates, commercially available AuCl3/CuI as catalysts, and O2 from air as the sole oxidant. This catalytic system provided unique selectivity for N-Boc amines in good yields. More significantly, gram-scale preparation of medicinally important N-Boc amine intermediates was successfully implement, which demonstrated a potential application prospect in industrial syntheses. Furthermore, this approach also showed good compatibility with tertiary and other useful alcohols. Investigations of the mechanisms revealed that gold catalyzed the reaction and copper acted as electron transfer mediator in the catalytic cycle.

COMPOUNDS AND COMPOSITIONS FOR THE TREATMENT OF PARASITIC DISEASES

The present invention provides a compound of formula (Ia) or a pharmaceutically acceptable salt thereof; a method for manufacturing the compounds of the invention, solid forms, combinations of pharmacologically active agents, pharmaceutical compositions and methods of using such compounds and solid forms thereof to treat or prevent parasitic diseases, for example malaria.

Iodoarene-Catalyzed Oxyamination of Unactivated Alkenes to Synthesize 5-Imino-2-Tetrahydrofuranyl Methanamine Derivatives

Reported here is the room-temperature metal-free iodoarene-catalyzed oxyamination of unactivated alkenes. In this process, the alkenes are difunctionalized by the oxygen atom of the amide group and the nitrogen in an exogenous HNTs2 molecule. This mild and open-air reaction provided an efficient synthesis to N-bistosyl-substituted 5-imino-2-tetrahydrofuranyl methanamine derivatives, which are important motifs in drug development and biological studies. Mechanistic study based on experiments and density functional theory calculations showed that this transformation proceeds via activation of the substrate alkene by an in situ generated cationic iodonium(III) intermediate, which is subsequently attacked by an oxygen atom (instead of nitrogen) of amides to form a five-membered ring intermediate. Finally, this intermediate undergoes an SN2 reaction by NTs2 as the nucleophile to give the oxygen and nitrogen difunctionalized 5-imino-2-tetrahydrofuranyl methanamine product. An asymmetric variant of the present alkene oxyamination using chiral iodoarenes as catalysts also gave promising results for some of the substrates.

Design and Synthesis of 56 Shape-Diverse 3D Fragments

Fragment-based drug discovery is now widely adopted for lead generation in the pharmaceutical industry. However, fragment screening collections are often predominantly populated with flat, 2D molecules. Herein, we describe a workflow for the design and synthesis of 56 3D disubstituted pyrrolidine and piperidine fragments that occupy under-represented areas of fragment space (as demonstrated by a principal moments of inertia (PMI) analysis). A key, and unique, underpinning design feature of this fragment collection is that assessment of fragment shape and conformational diversity (by considering conformations up to 1.5 kcal mol?1 above the energy of the global minimum energy conformer) is carried out prior to synthesis and is also used to select targets for synthesis. The 3D fragments were designed to contain suitable synthetic handles for future fragment elaboration. Finally, by comparing our 3D fragments with six commercial libraries, it is clear that our collection has high three-dimensionality and shape diversity.

Preparation method of 2-(4-piperidyl)-2-propanol and hydrochloride thereof

The invention provides a preparation method of 2-(4-piperidyl)-2-propanol and hydrochloride thereof. The method comprises the following steps: introducing tert-butyloxycarboryl as an amino protectiongroup on a raw material 4-piperidinecarboxylate molecule, carrying out alkylation addition on an ester group in the raw material molecule by using a methyl Grignard reagent, removing a BOC protectiongroup in an acidolysis manner to obtain 2-(4-piperidinyl)-2-propanol hydrochloride, and adding an alkali to adjust the pH value in order to obtain 2-(4-piperidinyl)-2-2-propanol. The preparation method provided by the invention is simple, easy to operate and high in yield, has the cost advantage and is very suitable for industrial production.

C10-ALKYLENE SUBSTITUTED 13-MEMBERED MACROLIDES AND USES THEREOF

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Light-Mediated Formal Radical Deoxyfluorination of Tertiary Alcohols through Selective Single-Electron Oxidation with TEDA2+.

The synthesis of tertiary alkyl fluorides through a formal radical deoxyfluorination process is described herein. This light-mediated, catalyst-free methodology is fast and broadly applicable allowing for the preparation of C?F bonds from (hetero)benzylic, propargylic, and non-activated tertiary alcohol derivatives. Preliminary mechanistic studies support that the key step of the reaction is the single-electron oxidation of cesium oxalates—which are readily available from the corresponding tertiary alcohols—with in situ generated TEDA2+. (TEDA: N-(chloromethyl)triethylenediamine), a radical cation derived from Selectfluor.

SPIRO-LACTAM NMDA RECEPTOR MODULATORS AND USES THEREOF

Disclosed are compounds having potency in the modulation of NMDA receptor activity. Such compounds can be used in the treatment of conditions such as depression and related disorders as well as other disorders.

Copper-Catalyzed and Indium-Mediated Methoxycarbonylation of Unactivated Alkyl Iodides with Balloon CO

This work emphasizes the synthesis of alkyl esters via Cu-catalyzed and In-mediated alkoxycarbonylation of unactivated alkyl iodides in the presence of In or InI. The reactions were suitable for the preparation of primary, secondary, and even tertiary alkyl esters, representing an exceptionally rare example for the creation of quaternary carbon centers upon formation of esters. The preliminary mechanistic studies indicated that alkyl radicals were involved, and Cu/In/CO played a cooperative role in the carbonylation event.

INHIBITORS OF THE RENAL OUTER MEDULLARY POTASSIUM CHANNEL

The present invention provides compounds of Formula I and the pharmaceutically acceptable salts thereof, which are inhibitors of the ROMK (Kir1.1) channel. The compounds may be used as diuretic and/or natriuretic agents and for the therapy and prophylaxis of medical conditions including cardiovascular diseases such as hypertension, heart failure and chronic kidney disease and conditions associated with excessive salt and water retention.