106498-32-2

Usage

Uses

An intermediate in the process for producing optically active Flurbiprofen (F598700).

Upstream product

• 78019-48-4 (2E,4R)-5-methyl-4-phenylhex-2-ene 
• 84519-63-1 (R,E)-4-phenyl-3-buten-2-yl acetate 
• 586341-95-9 (3S,4E)-2-methyl-3-phenylhex-4-enoic acid 
• 586341-96-0 (3S,4E)-2-methyl-3-phenylhex-4-en-1-ol 
• 19643-71-1 (2S)-3-methyl-2-phenylbutan-1-ol 
• 62413-47-2 (2R,3E)-4-phenyl-3-buten-2-ol 
• 36004-04-3 ethyl (E)-1-phenylbut-1-en-3-ol 

Downstream Products

• 267013-77-4 (S)-3-methyl-2-phenylbutylammonium (R)-2-hydroxy-4-phenylbutanoate 

Relevant academic research and scientific papers

Enantioselective synthesis of benzylic stereocentres via Claisen rearrangement of enantiomerically pure allylic alcohols: Preparation of (R)- and (S)-3-methyl-2-phenylbutylamine

The Johnson-Claisen rearrangement of enantiopure allylic alcohols in triethylorthopropionate is the key step for the preparation of chiral molecules with benzylic stereogenic carbon atoms bearing an isopropyl moiety. The synthetic procedure is applied to the preparation of (R)- and (S)-3-methyl-2-phenylbutylamine.

Process for optically resolving 2-(3-benzoylphenyl) propionic acid

Provided is a process for separating (S)- or (R)-2-(3-benzoylphenyl)propionic acid from a mixture of (S)- and (R)-2-(3-benzoylphenyl)propionic acid, which comprises (1) reacting the mixture of (S)- and (R)-2-(3-benzoylphenyl)propionic acid with (S)- or (R)-3-methyl-2-phenylbutylamine in a suitable solvent to form a diastereomer salt of (S)-2-(3-benzoylphenyl)propionic acid with (S)-3-methyl-2-phenylbutylamine or a diastereomer salt of (R)-2-(3-benzoylphenyl)propionic acid with (R)-3-methyl-2-phenylbutylamine; (2) separating the diastereomer salt from the reaction mixture; and (3) liberating the separated diastereomer salt to give (S)- or (R)-2-(3-benzoylphenyl)propionic acid. According to the present process, it is possible to obtain optically active (S)- or (R)-2-(3-benzoylphenyl)propionic acid having 99% or more of high optical purity in a high yield. Thus, the present process is a practical and efficient process which can simplify purification steps and can be applied for an industrial production process.