144433-72-7

Basic information

• Product Name: N-benzyloxycarbonyl-cis-2(R)-(acetoxymethyl)-6(S)-(hydroxymethyl)piperidine
• Synonyms: N-benzyloxycarbonyl-cis-2(R)-(acetoxymethyl)-6(S)-(hydroxymethyl)piperidine
• CAS NO: 144433-72-7
• Molecular Weight: 321.373
• Mol File: 144433-72-7.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: N-benzyloxycarbonyl-cis-2(R)-(acetoxymethyl)-6(S)-(hydroxymethyl)piperidine(CAS DataBase Reference)
• NIST Chemistry Reference: N-benzyloxycarbonyl-cis-2(R)-(acetoxymethyl)-6(S)-(hydroxymethyl)piperidine(144433-72-7)
• EPA Substance Registry System: N-benzyloxycarbonyl-cis-2(R)-(acetoxymethyl)-6(S)-(hydroxymethyl)piperidine(144433-72-7)

Safety Data

• Hazardous Substances Data: 144433-72-7(Hazardous Substances Data)

Upstream product

• 108-05-4 vinyl acetate 
• 144433-70-5 N-carbobenzoxy-cis-2,6-bis(hydroxymethyl)piperidine 
• 59234-43-4 meso-1-((benzyloxy)carbonyl)piperidine-2,6-dicarboxylic acid 
• 144433-68-1 cis-(N-benzyloxycarbonyl)-2,6-di-carboxymethyl piperidine 
• 501-53-1 benzyl chloroformate 
• 138-60-3 chelidamic acid 
• 499-83-2 Pyridine-2,6-dicarboxylic acid 
• 59234-46-7 dimethyl (2R,6S)-piperidine-2,6-dicarboxylate 
• 144433-71-6 N-benzyloxycarbonyl-cis-2,6-(acetoxymethyl)piperidine 

Downstream Products

• 182816-37-1 (-)-N-(benzyloxycarnonyl)-cis-2(R)-(acetoxymethyl)-6(S)-<(methoxymethoxy)methyl>piperidine 
• 177473-32-4 ((2R,6R)-1-Benzyl-6-methyl-piperidin-2-yl)-methanol 
• 177473-33-5 (2R,6R)-1-Benzyl-6-methyl-piperidine-2-carbaldehyde 
• 182816-40-6 (+)-N-(benzyloxycarnonyl)-cis-6(S)-<(methoxymethoxy)methyl>piperidine-2(R)-carboxylic acid 
• 182816-38-2 (-)-N-(benzyloxycarnonyl)-cis-2(S)-<(methoxymethoxy)methyl>-6(R)-(hydroxymethyl)piperidine 
• 177341-38-7 (2R,6S)-2-Acetoxymethyl-6-methanesulfonyloxymethyl-piperidine-1-carboxylic acid benzyl ester 
• 144433-73-8 (2R,6S)-2-Acetoxymethyl-6-(tert-butyl-dimethyl-silanyloxymethyl)-piperidine-1-carboxylic acid benzyl ester 

Relevant articles and documents

Cis-2,6-Bis-(methanolate)-piperidine oxovanadium(V) complexes as catalysts for oxidative alkenol cyclization by tert-butyl hydroperoxide

cis-2,6-Bis-(methanolate)-piperidine oxovanadium(V) complexes are Lewis acids able to catalyze oxidative cyclization of alkenols by tert-butyl hydroperoxide (TBHP). Terminal dimethyl-substituted (prenyl-type) 4-pentenols bearing an alkyl or a phenyl group in position 1 afford under such conditions 2,5-cis-derivatives of 2-(tetrahydrofuran-2-yl)-2-propanol as major and tetrahydropyran-3-ols as minor products (four examples). Oxidizing 1-phenyl-6-methylhept-5-en-1-ol yields a 75/25-mixture of the derived 2-(tetrahydropyran-2-yl)-2-propanol and an oxepan-3-ol, whereas 2-propenols give epoxides in up to 94% yield. Epoxidizing geraniol by TBHP in the presence of a vanadium catalyst prepared from (2S,6R)-2-diphenylmethanol-6- hydroxymethylpiperidine occurs enantioselectively. Highfield shifts of vanadium-51 resonances upon adding alkyl hydroperoxides to solutions of cis-2,6-bis-(methanolate)-piperidine vanadium(V) complexes point to vanadium(V) tert-butyl peroxy complex formation as key step for activating peroxides.

Enzymatic route to chiral, nonracemic cis-2,6- and cis,cis-2,4,6-substituted piperidines. Synthesis of (+)-dihydropinidine and dendrobate alkaloid (+)-241D

Piperidine-based compounds are an important class of natural alkaloids found in plants, insects, and amphibians. A general asymmetric synthesis of 2-alkyl-6-methylpiperidines is presented via the enzymatic desymmetrization of meso cis-2,6- and cis,cis-2,4,6-substituted piperidines with Aspergillus niger lipase (ANL). The enzymatic reaction proceeds in excellent chemical yield and high enantiotopic selectivity (ee ≥ 98%). The general method is used to effect the synthesis of (±)-dihydropinidine-HCl as well as the first asymmetric synthesis of dendrobate alkaloid (+)-241D.