164456-75-1

Usage

Uses

Used in Pharmaceutical Industry:
R-METHYL 1-BOC-PIPERIDINE-2-CARBOXYLATE is used as a synthetic intermediate for the development of various pharmaceuticals. Its functional groups and protecting group make it a valuable component in the synthesis of drugs with specific therapeutic properties.
Used in Agrochemical Industry:
In the agrochemical sector, R-METHYL 1-BOC-PIPERIDINE-2-CARBOXYLATE is used as a precursor in the synthesis of agrochemicals. Its structural features contribute to the creation of compounds with pesticidal or herbicidal activities, enhancing crop protection and yield.
Used in Organic Synthesis:
R-METHYL 1-BOC-PIPERIDINE-2-CARBOXYLATE is employed as a key building block in organic synthesis. Its versatility allows for the creation of a wide range of chemical compounds, expanding the scope of chemical research and development.
Used in Medicinal Chemistry Research:
R-METHYL 1-BOC-PIPERIDINE-2-CARBOXYLATE is utilized in medicinal chemistry research as a starting material for the design and synthesis of new bioactive molecules. Its unique structure and functional groups facilitate the exploration of novel therapeutic agents and drug candidates.

Upstream product

• 1723-00-8 (R)-(+)-pipecolic acid 
• 24424-99-5 di-tert-butyl dicarbonate 
• 35677-83-9 (+)-2R-Piperidine-2-carboxylic acid methyl ester 
• 18650-38-9 (R)-piperidine-2-carboxylic acid methyl ester hydrochloride 
• 1538-75-6 2,2-dimethylpropanoic anhydride 
• 186581-53-3 diazomethane 
• 28697-17-8 N-BOC-D-pipecolic acid 
• 1013212-42-4 tert-butyl 1-(R)-2-((S)-1,2-dihydroxylethyl)piperidine-1-carboxylate 
• 75844-69-8 t-butyl piperidinecarboxylate 
• 79-22-1 methyl chloroformate 
• 123387-55-3 1-t-butoxycarbonyl-2-tributylstannylpiperidine 
• 98303-20-9 1-(tert-butoxycarbonyl)piperidine-2-carboxylic acid 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 768-33-2 phenyldimethylsilyl chloride 

Downstream Products

• 28697-17-8 N-BOC-D-pipecolic acid 
• 134441-61-5 tert-butyl (2R)-2-(hydroxymethyl)piperidine-1-carboxylate 
• 134526-69-5 tert-butoxycarbonyl-D-piperidine-2-carboxaldehyde 

Relevant academic research and scientific papers

Catalytic asymmetric hydrogenation of 1-aza-2-cycloalkene-2-carboxylates catalyzed by a trans-chelating chiral diphosphine PhTRAP-rhodium complex

A rhodium complex coordinated with a trans-chelating chiral diphosphine (S,S)-(R,R)-PhTRAP was an effective catalyst for asymmetric hydrogenation of N-acyl-1-aza-2-cycloalkene-2-carboxylates, which gave the corresponding protected cyclic α-amino acids wit

X-ray Structure-Guided Discovery of a Potent, Orally Bioavailable, Dual Human Indoleamine/Tryptophan 2,3-Dioxygenase (hIDO/hTDO) Inhibitor That Shows Activity in a Mouse Model of Parkinson’s Disease

Human indoleamine 2,3-dioxygenase 1 (hIDO1) and tryptophan 2,3-dioxygenase (hTDO) have been closely linked to the pathogenesis of Parkinson’s disease (PD); nevertheless, development of dual hIDO1 and hTDO inhibitors to evaluate their potential efficacy against PD is still lacking. Here, we report biochemical, biophysical, and computational analyses revealing that 1H-indazole-4-amines inhibit both hIDO1 and hTDO by a mechanism involving direct coordination with the heme ferrous and ferric states. Crystal structure-guided optimization led to23, which manifested IC50values of 0.64 and 0.04 μM to hIDO1 and hTDO, respectively, and had good pharmacokinetic properties and brain penetration in mice.23showed efficacy against the 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-induced mouse motor coordination deficits, comparable to Madopar, an anti-PD medicine. Further studies revealed that different from Madopar,23likely has specific anti-PD mechanisms involving lowering IDO1 expression, alleviating dopaminergic neurodegeneration, reducing inflammatory cytokines and quinolinic acid in mouse brain, and increasing kynurenic acid in mouse blood.

Synthesis and biological evaluation of (-)-6-O-desmethylcryptopleurine and analogs

(-)-Cryptopleurine 1 is one of the most potent anti-proliferative member of the phenanthroquinolizidine class of alkaloids. We report here the synthesis of (-)-6-O-desmethylcryptopleurine (-)-2 and (-)-6-O-desmethyl-(15R)-hydroxycryptopleurine (-)-4 in th

Asymmetric lithiation trapping of N -boc heterocycles at temperatures above -78°C

The asymmetric lithiation trapping of N-Boc heterocycles using s-BuLi/chiral diamines at temperatures up to -20°C is reported. Depending on the N-Boc heterocycle, lithiation is accomplished using s-BuLi and (-)-sparteine or the (+)-sparteine surrogate in the temperature range -50 to -20°C for short reaction times (2-20 min). Subsequent electrophilic trapping or transmetalation-Negishi coupling delivered functionalized N-Boc heterocycles in 47-95% yield and 77:23-93:7 er. With N-Boc pyrrolidine, trapped products can be generated in ～90:10 er even at -20°C.

Organocatalytic one-pot oxidative cleavage of terminal diols to dehomologated carboxylic acids

The organocatalytic one-pot oxidative cleavage of terminal 1,2-diols to one-carbon-unit-shorter carboxylic acids is described. The combination of 1-Me-AZADO (cat.), NaOCl (cat.), and NaClO2 caused smooth one-pot oxidative cleavage under mild conditions. A broad range of substrates including carbohydrates and N-protected amino diols were converted without epimerization. Terminal triols and tetraols respectively underwent cleavage of their C-2 and C-3 moieties to afford their corresponding two- and three-carbon-unit-shorter carboxylic acids.

Nitroxyl radical/PhI(OAc)2: One-pot oxidative cleavage of vicinal diols to (di)carboxylic acids

A mild and user-friendly one-pot oxidative cleavage of vicinal diols to their corresponding (di)carboxylic acids using AZADOs and PhI(OAc)2 is described. 1,2-Diols and 2,3-diols as well as 1,2,3-triol gave one- or two-carbon-unit-shorter carboxylic acids. Internal vicinal diols also smoothly underwent one-pot oxidative cleavage to afford the corresponding dicarboxylic acids. Cyclic vicinal diols are converted to their corresponding open-form dicarboxylic acids.

Highly enantioselective catalytic dynamic resolution of N-boc-2-lithiopiperidine: Synthesis of (R)-(+)- N-boc-pipecolic acid, (S)-(-)-coniine, (S)-(+)-pelletierine, (+)-β-conhydrine, and (S)-(-)-ropivacaine and formal synthesis of (-)-lasubine II and (+)-cermizine C

The catalytic dynamic resolution (CDR) of rac-2-lithio-N-Boc-piperidine using chiral ligand 8 or its diastereomer 9 in the presence of TMEDA has led to the highly enantioselective syntheses of both enantiomers of 2-substituted piperidines using a wide range of electrophiles. The CDR has been applied to the synthesis of (R)- and (S)-pipecolic acid derivatives, (+)-β-conhydrine, (S)-(+)-pelletierine, and (S)-(-)-ropivacaine and the formal synthesis of ()-lasubine II and (+)-cermizine C.

Asymmetric deprotonation of N -boc piperidine: React IR monitoring and mechanistic aspects

The high yielding asymmetric deprotonation trapping of N-Boc piperidine is successfully realized using s-BuLi and a (+)-sparteine surrogate. Monitoring of the lithiation by in situ React IR allowed the direct observation of a prelithiation complex.

MGLUR5 MODULATORS II

The present invention is directed to novel compounds, to a process for their preparation, their use in therapy and pharmaceutical compositions comprising the novel compounds.

MGluR5 modulators I

The present invention is directed to novel compounds, to a process for their preparation, their use in therapy and pharmaceutical compositions comprising the novel compounds.