Indane Derivative Intermediates for Perfume Synthesis

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Solution Overview

Problem

Current methods for producing perfuming ingredients, such as those described in EP 1022265, face challenges with low yield and productivity due to lengthy processes and the need for different key intermediates, limiting the efficiency of perfumery processes.

Innovation Solution

A new process involving the reduction and hydrolysis of specific precursor compounds, including those of formula (I) and (II), to obtain perfuming ingredients with higher yield and productivity, utilizing stereoisomers and various alkyl groups, and employing catalysts like supported Pd for hydrogenation and solvents like carboxylic acids for improved reaction conditions.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If the prior art process (EP 1022265) is used to produce perfuming ingredients, then the production can be achieved, but the yield and productivity are low due to lengthy processes and poor productivity

Engineering Contradiction:
ImproveproductivityVSAvoidprocess time
Core Design Contradiction:
ProductivityVSLoss of time

Solution Approach 1:

The patent applies preliminary action by pre-functionalizing the indane derivative with a hydroxymethyl group and ester group in specific positions before the final transformation. This preliminary structuring of the intermediate compound (I) with specific substituents R1 at positions 4, 5, 6, or 7 enables a more direct and efficient conversion to the target perfuming ingredient, avoiding the need for multiple subsequent modification steps required by prior art processes.

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The patent employs parameter changes by systematically varying the substituents R1 (which can be hydrogen, alkyl, alkoxy, halogen, or their combinations) on the indane core structure. This parametric approach allows optimization of both the intermediate stability and final product performance, while the systematic variation enables identification of high-yield pathways that improve productivity compared to fixed prior art routes.

Inventive Principle:
Principle #35Parameter changes

2Quantity of substance

If the prior art process is used, then production can proceed, but the overall yield is poor and the process requires very different key intermediates

Engineering Contradiction:
ImproveyieldVSAvoidprocess complexity
Core Design Contradiction:
Quantity of substanceVSDevice complexity

Solution Approach 1:

The patent achieves universality by designing a platform intermediate (I) with a versatile core structure that can serve multiple synthetic purposes. The indane derivative with hydroxymethyl and ester groups, substituted with various R1 groups, functions as a universal precursor that can be transformed into different perfuming ingredients by simple variation of conditions, eliminating the need for completely different key intermediates required by prior art for different target molecules.

Inventive Principle:
Principle #6Universality (Multi-functionality)

Solution Approach 2:

The patent applies the extraction principle by isolating and optimizing the specific functional pattern (hydroxymethyl group at position 2 and ester group at position 1) from the complex prior art synthesis routes. This extracted functional motif becomes the core of intermediate (I), which can then be efficiently converted to target products without carrying forward the unnecessary complexity and multiple steps of the original synthesis pathways.

Inventive Principle:
Principle #2Taking out (Extraction)

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

The new process significantly enhances the yield and productivity of perfuming ingredients, offering a more efficient route compared to existing methods by optimizing reaction conditions and intermediate usage.

Implementation Method 1

utilizing stereoisomers and various alkyl groups, and employing catalysts like supported Pd for hydrogenation

Methodology Applied
Scientific EffectHydrogenation: Hydrogenation

Implementation Method 2

employing catalysts like supported Pd for hydrogenation

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 3

A new process involving the reduction and hydrolysis of specific precursor compounds

Methodology Applied
Scientific EffectHydrolysis: Hydrolysis

Data Source

PatentEP3245185B1Intermediate compounds for producing perfuming ingredients
Publication Date: 2019.03.13 FIRMENICH SA
  • EP3245185B1 patent drawing
  • EP3245185B1 patent drawing
  • EP3245185B1 patent drawing

AI summary

The present invention relates to the field of chemical processes and, more particularly, it concerns valuable new chemical intermediates of formula (IV) for producing perfuming ingredients.