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
• Article Data: 4

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

2,3-Diacetoxy-N-benzyloxycarbonylpiperidine (cas# 92599-77-4) is a compound useful in organic synthesis.

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

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

Downstream Products

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

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.

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.