951698-15-0

Usage

Uses

Used in Pharmaceutical Research:
5-Isoxazolemethanamine, .alpha.-ethenyl-N,N-dimethylis utilized as a key building block in the development of new pharmaceuticals. Its unique structure allows for the creation of a variety of drug candidates that can target specific biological pathways or receptors.
Used in Organic Synthesis:
In the field of organic synthesis, 5-Isoxazolemethanamine, .alpha.-ethenyl-N,N-dimethyl- serves as an important intermediate. Its reactivity and functional groups make it suitable for the synthesis of a range of organic compounds, including complex molecules with potential applications in various industries.
Used in Agrochemical Development:
5-Isoxazolemethanamine, .alpha.-ethenyl-N,N-dimethylalso has potential applications in the agrochemical industry. It can be used in the development of new pesticides or other agrochemicals that can improve crop yields and protect plants from diseases and pests.
Used as a Reagent in Chemical Reactions:
Due to its reactive nature, 5-Isoxazolemethanamine, .alpha.-ethenyl-N,N-dimethyl- can act as a reagent in various chemical reactions. It can facilitate the formation of new chemical bonds or aid in the transformation of other compounds, making it a valuable tool in research laboratories.
Used as a Precursor to Other Functionalized Compounds:
Given its structural features, 5-Isoxazolemethanamine, .alpha.-ethenyl-N,N-dimethylcan be employed as a precursor to synthesize other functionalized compounds. This makes it a versatile starting material for the production of specialty chemicals with specific applications across different sectors.

Upstream product

• 124-40-3 dimethyl amine 
• 951698-14-9 C₁₃H₁₃NO₃ 
• 124-63-0 methanesulfonyl chloride 
• 50-00-0 formaldehyd 
• 951698-16-1 C₁₃H₁₃NO₃ 
• 2552-53-6 3-benzyloxy-isoxazole-5-carbaldehyde 
• 951698-18-3 C₁₅H₁₅NO₄ 

Downstream Products

• 951698-19-4 C₁₅H₁₇IN₂O₂ 

Relevant academic research and scientific papers

Process Research and Development of an Enantiomerically Enriched Allyic Amine, One of the Key Intermediates for the Manufacture of Synthetic Tetracyclines

A robust, cost-effective, and high yielding manufacturing process for enantiomerically enriched (S)-allylic amine 3, a key intermediate for fully synthetic tetracyclines have been developed. Two novel and scalable asymmetric vinylations resulting in high-to-excellent stereoselectivity have been developed for the key step. The final product is purified by an efficient crystallization of a l-tartaric salt. The process described has been used to manufacture ～350 kg of the tartaric salt of 3 with 99.0% ee in 8 steps (35% overall yield) from cheap and readily available dimethyl maleate.

SYNTHESIS OF ENONE INTERMEDIATE

The tetracycline class of antibiotics has played a major role in the treatment of infectious diseases for the past 50 years. However, the increased use of the tetracyclines in human and veterinary medicine has led to resistance among many organisms previously susceptible to tetracycline antibiotics. The recent development of a modular synthesis of tetracycline analogs through a chiral enone intermediate has allowed for the efficient synthesis of novel tetracycline analogs never prepared before. The present invention provides a more efficient route for preparing the enone intermediate.

A practical, enantioselective synthetic route to a key precursor to the tetracycline antibiotics

A practical, enantioselective synthetic route to a key precursor to the tetracycline antibiotics is reported. The route proceeds in nine steps (21% yield) from the commercial substance methyl 3-hydroxy-5-isoxazolecarboxylate. Key steps in the route involve enantioselective addition of divinylzinc to 3-benzyloxy-5-isoxazolecarboxaldehyde and an endo-selective intramolecular furan Diels-Alder cycloaddition reaction. The route described has provided more than 40 g of chromatographically pure 1 with 93% ee.