57728-40-2

Usage

Uses

Used in Pharmaceutical Industry:
(-)-2-amino-3-methyl-1,1-diphenylbutanol is used as an analgesic for the treatment of severe or persistent pain. Its opioid properties provide effective pain relief, making it a valuable component in pain management therapies.
(-)-2-amino-3-methyl-1,1-diphenylbutanol is also used as an antitussive agent for the management of cough. Its ability to suppress cough reflexes helps alleviate symptoms associated with respiratory conditions and provides relief to patients experiencing persistent coughing.
As a Schedule II controlled substance, levomethorphan's potential for abuse and dependence necessitates its prescription and administration under the supervision of a healthcare professional. Common side effects associated with its use include dizziness, drowsiness, nausea, constipation, and respiratory depression.

Upstream product

• 57728-51-5 2-[1-(Hydroxy-diphenyl-methyl)-2-methyl-propylamino]-cyclopent-1-enecarbonitrile 
• 591-50-4 iodobenzene 
• 5619-05-6 DL-valine methyl ester hydrochloride 
• 13893-45-3 valine ethyl ester 
• 57728-20-8 2-(2-Cyano-cyclopent-1-enylamino)-3-methyl-butyric acid ethyl ester 

Downstream Products

• 13742-09-1 3-methyl-1,2-diphenylbutan-1-one 
• 78603-95-9 1,1-diphenyl-L-valinol 
• 86695-06-9 (R)-(+)-2-amino-3-methyl-1,1-diphenylbutan-1-ol 

Relevant academic research and scientific papers

Synthesis of Highly Stereodefined Tetrasubstituted Acyclic All-Carbon Olefins via a Syn-Elimination Approach

An efficient synthesis of stereodefined tetrasubstituted acyclic all-carbon olefins has been developed via a bis(2,6-xylyl)phosphate formation of stereoenriched tertiary alcohols, followed by in situ syn-elimination of the corresponding phosphates under mild conditions. This chemistry tolerates a wide variety of electronically and sterically diverse substrates and generates the desired tetrasubstituted olefins in high yields and stereoselectivities (>95:5) in most cases. This stereocontrolled olefin synthesis has been applied to the synthesis of anticancer drug tamoxifen in three steps from commercially available 1,2-diphenylbutan-1-one in 97:3 stereoselectivity and 78% overall yield.

Highly Stereoselective Synthesis of Tetrasubstituted Acyclic All-Carbon Olefins via Enol Tosylation and Suzuki-Miyaura Coupling

A highly stereocontrolled synthesis of tetrasubstituted acyclic all-carbon olefins has been developed via a stereoselective enolization and tosylate formation, followed by a palladium-catalyzed Suzuki-Miyaura cross-coupling of the tosylates and pinacol boronic esters in the presence of a Pd(OAc)2/RuPhos catalytic system. Both the enol tosylation and Suzuki-Miyaura coupling reactions tolerate an array of electronically and sterically diverse substituents and generate high yield and stereoselectivity of the olefin products. Judicious choice of substrate and coupling partner provides access to either the E- or Z-olefin with excellent yield and stereochemical fidelity. Olefin isomerization was observed during the Suzuki-Miyaura coupling. However, under the optimized cross-coupling reaction conditions, the isomerization was suppressed to 5% in most cases. Mechanistic probes indicate that the olefin isomerization occurs via an intermediate, possibly a zwitterionic palladium carbenoid species.

Tandem reduction and host-guest complexation

The present invention relates to a tandem process of reduction and host-guest complexation using metal-hydride complexes to reduce chemical entities bearing carbonyl groups or their equivalents, and host-guest complexation to achieve improved optical resolution of the reduction product. In the complexation step, the reduction product is optically resolved via inclusion into the crystalline complex where it resides as guest and another complex component acts as host. Additional crystallization stages are performed if further improvements in the enantiomeric excess is desired.