251107-37-6

Basic information

• Product Name: 1-Piperidinecarboxylic acid, 4-(phenylmethyl)-, 1,1-dimethylethyl ester
• Synonyms: 1-Piperidinecarboxylic acid, 4-(phenylmethyl)-, 1,1-dimethylethyl ester;tert-butyl 4-benzylpiperidine-1-carboxylate
• CAS NO: 251107-37-6
• Molecular Formula: C₁₇H₂₅NO₂
• Molecular Weight: 275.3859
• Mol File: 251107-37-6.mol

Chemical Properties

• Boiling Point: 370.0±11.0 °C(Predicted)
• Appearance: /
• Density: 1.047±0.06 g/cm3(Predicted)
• PKA: -1.28±0.40(Predicted)
• CAS DataBase Reference: 1-Piperidinecarboxylic acid, 4-(phenylmethyl)-, 1,1-dimethylethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Piperidinecarboxylic acid, 4-(phenylmethyl)-, 1,1-dimethylethyl ester(251107-37-6)
• EPA Substance Registry System: 1-Piperidinecarboxylic acid, 4-(phenylmethyl)-, 1,1-dimethylethyl ester(251107-37-6)

Safety Data

• Hazardous Substances Data: 251107-37-6(Hazardous Substances Data)

Usage

Molecular weight

279.36 g/mol

Appearance

White solid

Stability

Stable under normal conditions

Handling and storage

Easily handled and stored

Main application

Pharmaceutical research (production of drugs and natural products)

Other applications

Production of agrochemicals and other fine chemicals

Use as a reagent

Commonly used in organic synthesis

Derivative of

Piperidine (heterocyclic amine)

Utilization

As a protecting group for amines in peptide synthesis

Upstream product

• 24388-23-6 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole 
• 145508-94-7 tert-butyl 4-(iodomethyl)piperidine-1-carboxylate 
• 31252-42-3 4-benzylpyperidine 
• 201230-82-2 carbon monoxide 
• 75-65-0 tert-butyl alcohol 
• 24424-99-5 di-tert-butyl dicarbonate 
• 544478-05-9 4-benzyl-N-tritylpiperidine 
• 100-39-0 benzyl bromide 
• 375853-82-0 tert-Butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-1(2H)-pyridinecarboxylate 
• 100-59-4 phenylmagnesium chloride 
• 23418-91-9 9-phenyl-9-borabicyclo[3.3.1]nonane 

Downstream Products

• 251107-38-7 tert-butyl 4-benzyl-2-methylpiperidine-1-carboxylate 

Relevant articles and documents

Merging Halogen-Atom Transfer (XAT) and Copper Catalysis for the Modular Suzuki-Miyaura-Type Cross-Coupling of Alkyl Iodides and Organoborons

We report here a mechanistically distinct approach to achieve Suzuki-Miyaura-type cross-couplings between alkyl iodides and aryl organoborons. This process requires a copper catalyst but, in contrast with previous approaches based on palladium and nickel

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.

Practical synthesis of pharmaceutically relevant molecules enriched in sp3 character

The expedient synthesis of compounds enriched in sp3 character is key goal in modern drug discovery. Herein, we report how a single pot Suzuki-Miyaura-hydrogenation can be used to furnish lead and fragment-like products in good to excellent yields. The approach has been successfully applied in formats amenable to parallel synthesis, in an asymmetric sense, and in the preparation of molecules with annotated biological activity.

Suzuki-miyaura cross-coupling reactions of unactivated alkyl halides catalyzed by a nickel pincer complex

A nickel(II) pincer complex, [(MeN2N)Ni-Cl], was used to catalyze alkyl-alkyl and alkyl-aryl Suzuki-Miyaura coupling reactions of unactivated alkyl halides. The coupling of 9-alkyl-9-borabicyclo[3.3.1]nonane and 9-phenyl-9-borabicyclo[3.3.1]nonane reagents with alkyl halides was achieved in modest to good yields. The reactions tolerated a variety of useful functional groups including ester, ether, furan, thioether, acetal, and Boc groups. Georg Thieme Verlag Stuttgart, New York.

N-ureidoalkyl-piperidines as modulators of chemokine receptor activity

The present application describes modulators of CCR3 of formula (I): or pharmaceutically acceptable salt forms thereof, useful for the prevention of asthma and other allergic diseases.

Single-step conversion of N-benzyl, N-trityl and N-diphenylmethyl amines to t-butyl carbamates using polymethylhydrosiloxane

t-Butyl carbamates were obtained efficiently in high yields from the corresponding N-benzyl, N-trityl and N-diphenylmethyl precursors in a single-step reductive transformation employing polymethylhydrosiloxane and di-t-butyl dicarbonate under Pd(OH)2/C catalysis.

N-ureidoalkyl-piperidines as modulators of chemokine receptor activity

The present application describes modulators of CCR3 of formula (I): or pharmaceutically acceptable salt forms thereof, useful for the prevention of asthma and other allergic diseases.