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Synthetic Routes of 2,2'-Azanediylbis(1-(6-Fluorochroman-2-yl)Ethanol) Hydrochloride: A Comprehensive Review
In the world of chemistry, the synthesis of new compounds is a constant pursuit.
One such compound that has gained interest in recent years is 2,2'-azanediylbis(1-(6-fluorochroman-2-yl)ethanol) hydrochloride, which has various applications in the chemical industry.
This article provides a comprehensive review of the synthetic routes to this compound.
Background
2,2'-azanediylbis(1-(6-fluorochroman-2-yl)ethanol) hydrochloride, commonly referred to as HPC, is a synthetic chemical that has been widely used as a pharmaceutical intermediate, a research tool in biochemistry and molecular biology, and a building block in the synthesis of other chemicals.
Due to its versatile nature, there is a growing demand for this compound in the chemical industry, which has led to the development of various synthetic routes for its production.
Synthetic Routes
There are several synthetic routes to producing 2,2'-azanediylbis(1-(6-fluorochroman-2-yl)ethanol) hydrochloride, which can be broadly classified into organic and inorganic methods.
Organic Synthesis
The organic synthesis of HPC involves several steps, which can be classified into four main methods: the Sharpless epoxidation, the guanidine-based protocol, the Lossen rearrangement, and the Horner-Ebensen condensation.
- The Sharpless Epoxidation
The Sharpless epoxidation is a widely used method for the synthesis of HPC.
This method involves the use of a chiral catalyst, such as chiral tin (II) iodide, to epoxidize a primary alcohol, such as 1-(6-fluorochroman-2-yl)ethanol, to form a stereoisomeric mixture of the target compound.
The reaction mixture is then treated with hydrogen chloride to convert the epoxide to the corresponding hydrochloride salt.
Advantages: This method is efficient and provides a high yield of the target compound.
Disadvantages: The use of a chiral catalyst can be costly, and the process can be time-consuming.
- The Guanidine-Based Protocol
The guanidine-based protocol is another method for the synthesis of HPC.
This method involves the use of an excess of a guanidine compound, such as guanidine carbonate, to form a complex with the primary alcohol.
The complex is then treated with an oxidizing agent, such as potassium permanganate, to form the corresponding epoxide.
The epoxide is then hydrolyzed to form the target compound.
Advantages: This method is relatively inexpensive and can be performed without the use of chiral catalysts.
Disadvantages: The reaction can be difficult to control, and the yield of the target compound can be low.
- The Lossen Rearrangement
The Lossen rearrangement is a method for the synthesis of HPC that involves the use of a rearrangement reaction.
This method involves the conversion of a substituted cyclohexanone, such as 2-iodomethyl-3-fluoro-1-cyclohexanone, to the corresponding alcohol using a basic reagent, such as sodium hydroxide.
The alcohol is then converted to the target compound using a standard synthetic route, such as hydrolysis or epoxidation.
Advantages: This method provides a simple and efficient way to synthesize HPC.
Disadvantages: The synthesis of the cyclohexanone precursor can be difficult and time-consuming.
- The Horner-Ebensen Condensation
The Horner-Ebensen condensation is a method for the synthesis of HPC that involves the condensation of an aldehyde with an N-