Optical Resolution of (R)-1,1,3-Trimethyl-4-Aminoindane via Controlled Cooling
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Solution Overview
Problem
Conventional methods for producing (R)-1,1,3-trimethyl-4-aminoindane with high optical purity require repeated recrystallization of a salt obtained by optical resolution, resulting in low yield and are not industrially acceptable.
Innovation Solution
A method involving the steps of mixing 1,1,3-trimethyl-4-aminoindane, D-tartaric acid, and methanol, with the addition of water, followed by controlled cooling to produce a methanol solvate of D-tartrate of (R)-1,1,3-trimethyl-4-aminoindane, which is then filtered and treated with an alkali metal hydroxide solution to achieve high optical purity and yield.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Manufacturing precision
If repeated recrystallization is performed to achieve high optical purity, then optical purity is improved, but yield deteriorates
Solution Approach 1:
The invention changes the cooling rate parameter from conventional rapid cooling to controlled slow cooling (1-10°C/hour). This parameter change enables the formation of high-quality crystal structures during the cooling process, allowing the system to achieve both high optical purity through controlled crystallization and high yield by avoiding repeated recrystallization steps.
Solution Approach 2:
The invention utilizes the phase transition process during controlled cooling to transform the solution into a crystalline state. By controlling the cooling rate through the phase transition, the patent achieves selective crystallization of the desired enantiomer with high optical purity while maintaining high yield, eliminating the need for repeated recrystallization operations.
2Manufacturing precision
If conventional optical resolution method is used, then optical purity can be achieved, but process complexity increases due to repeated recrystallization
Solution Approach 1:
The invention performs preliminary action by controlling the cooling rate during the crystallization process to prevent the formation of unwanted crystal structures. This preliminary control during cooling eliminates the need for subsequent repeated recrystallization steps, thereby reducing process complexity while maintaining high optical purity.
Solution Approach 2:
The invention ensures continuity of useful action by maintaining a controlled cooling rate throughout the crystallization process. This continuous controlled cooling enables the system to proceed directly from solution to high-purity crystal formation in a single operation, eliminating the need for multiple discrete recrystallization steps and reducing overall process complexity.
Applied Scientific Principles
This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.
Function Achieved in This Case
This method enables the production of (R)-1,1,3-trimethyl-4-aminoindane with high optical purity and high yield, making it industrially advantageous.
Implementation Method 1
step (b) of cooling the obtained mixture; and step (c) of retrieving the methanol solvate of D-tartrate of (R)-1,1,3-trimethyl-4-aminoindane
Data Source
AI summary
A method for producing a methanol solvate of D-tartrate of (R)-1,1,3-trimethyl-4-aminoindane, the method comprising steps (a), (b), and (c) below, and comprising adding water to a reaction system before step (c): step (a) of mixing 1,1,3-trimethyl-4-aminoindane, D-tartaric acid, and methanol to provide a mixture containing a methanol solvate of D-tartrate of (R)-1,1,3-trimethyl-4-aminoindane; step (b) of cooling the obtained mixture; and step (c) of retrieving the methanol solvate of D-tartrate of (R)-1,1,3-trimethyl-4-aminoindane.