92599-77-4

Basic information

• Product Name: 2,3-Bis(acetyloxy)-1-piperidinecarboxylic Acid Phenylmethyl Ester
• Synonyms: 2,3-Bis(acetyloxy)-1-piperidinecarboxylic Acid Phenylmethyl Ester;2,3-Diacetoxy-N-benzyloxycarbonylpiperidine
• CAS NO: 92599-77-4
• Molecular Formula: C₁₇H₂₁NO₆
• Molecular Weight: 335.35
• Product Categories: Aromatics;Heterocycles
• Mol File: 92599-77-4.mol

Chemical Properties

• Boiling Point: 441.642°C at 760 mmHg
• Flash Point: 220.897°C
• Appearance: /
• Density: 1.248g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.546
• Solubility: Dichloromethane, Ethyl Acetate, Methanol
• PKA: -5.14±0.60(Predicted)
• CAS DataBase Reference: 2,3-Bis(acetyloxy)-1-piperidinecarboxylic Acid Phenylmethyl Ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-Bis(acetyloxy)-1-piperidinecarboxylic Acid Phenylmethyl Ester(92599-77-4)
• EPA Substance Registry System: 2,3-Bis(acetyloxy)-1-piperidinecarboxylic Acid Phenylmethyl Ester(92599-77-4)

Safety Data

• Hazardous Substances Data: 92599-77-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2,3-Bis(acetyloxy)-1-piperidinecarboxylic Acid Phenylmethyl Ester is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows for the development of new drugs with potential therapeutic applications, such as analgesics, anti-inflammatory agents, and other medications.
Used in Organic Synthesis:
In the field of organic synthesis, 2,3-Bis(acetyloxy)-1-piperidinecarboxylic Acid Phenylmethyl Ester serves as a key building block for the creation of complex organic molecules. Its functional groups can be selectively modified to produce a wide range of chemical products, including specialty chemicals, agrochemicals, and other industrial applications.
Used in Research and Development:
2,3-Bis(acetyloxy)-1-piperidinecarboxylic Acid Phenylmethyl Ester is also utilized in research and development settings to explore new chemical reactions and synthetic pathways. Its unique structure and reactivity make it an attractive candidate for studying novel synthetic strategies and developing innovative chemical processes.

InChI:InChI=1/C17H21NO6/c1-12(19)23-15-9-6-10-18(16(15)24-13(2)20)17(21)22-11-14-7-4-3-5-8-14/h3-5,7-8,15-16H,6,9-11H2,1-2H3

Upstream product

• 69622-67-9 benzyl 2-hydroxypiperidine-1-carboxylate 
• 106412-35-5 N-benzyloxycarbonyl-2-piperidone 
• 108-24-7 acetic anhydride 
• 473436-50-9 benzyl 2,3-dihydroxy-1-piperidinecarboxylate 
• 3742-91-4 N-(benzyloxycarbonyl)piperidine 
• 127-08-2 potassium acetate 

Downstream Products

• 473436-49-6 benzyl 2-oxooctahydrofuro[3,2-b]pyridine-4-carboxylate 
• 473436-52-1 benzyl 3-acetoxy-2-ethoxycarbonylmethyl-1-piperidinecarboxylate 

Relevant articles and documents

Synthesis of febrifugine derivatives and a solution to the puzzle of the structural determination of febrifugine

The stereo-structure of piperidine lactone (3), a synthetic intermediate of the antimalarial agent febrifugine ((+)-1) with a piperidine ring in the trans relative configuration, was re-revised to the cis-form. We determined that isomerization to the trans-form from the cis-form occurred in the stage (6 from 5) of deprotection in Baker's synthesis.

Re-revision of the stereo structure of piperidine lactone, an intermediate in the synthesis of febrifugine.

The stereo structure of piperidine lactone (3), an intermediate of the antimalarial agent febrifugine ((+)-1) prepared by a synthetic method, was re-revised to the cis-form from the trans-form.

Efficient synthesis of piperidine derivatives. Development of metal triflate-catalyzed diastereoselective nucleophilic substitution reactions of 2-methoxy- and 2-acyloxypiperidines

Nucleophilic substitution reactions of 2-methoxy- and 2-acyloxypiperidines were investigated. First, new and efficient methods for the preparation of the starting piperidine derivatives were developed. N-Benzyloxycarbonyl-2-methoxypiperidine (3) and 3-substituted-2-acyloxy-N-benzyloxycarbonylpiperidines (4a-d), which are recognized as the simplest imino-sugars, were prepared and were examined as substrates for nucleophilic substitution reactions with silyl enolates under the influence of catalytic amounts of metal triflates (Sc(OTf)3, Sn(OTf)2, Cu(OTf)2, Hf(OTf)4, etc). Among the triflates tested, Sc(OTf)3 gave the best results. It was found that 2-acetoxy-3-benzyloxy-N-benzyloxycarbonylpiperidine (4a) reacted with silyl enolates to afford the 2-alkylated adducts in high cis-selectivity, while 2,3-diacyloxy-N-benzyloxycarbonylpiperidines (4b-d) showed trans-selectivity. The stereochemical assignments were carefully performed using NMR analysis, X-ray crystallography, and synthetic transformations. Febrifugine (1), a potent antimalarial alkaloid, was successfully synthesized from 2,3-diacetoxy-N-benzyloxycarbonylpiperidine (4b) on the basis of these diastereoselective nucleophilic substitution reactions.

ACETOXYLATION OF PIPERIDINE DERIVATIVES AT THE 3-POSITION. STEREOSELECTIVE SYNTHESIS OF PSEUDOCONHYDRINE AND N-METHYLPSEUDOCONHYDRINE

Anodic oxidation of N-methoxycarbonylpipridine derivatives in AcOH gave 2,3-diacetoxylated products, which were shown to be useful intermediates for the stereoselective synthesis of 3-hydroxypiperidine derivatives including pseudoconhydrine and N-methylpseudoconhydrine, the Conium alcaloids.