188302-27-4

Upstream product

• 17640-15-2 methyl cyanoformate 
• 511283-89-9 4-(4-fluorophenyl)-1-methylpiperidine-2,6-dione 
• 511284-18-7 dimethyl-4-(4-fluorophenyl)-1-methyl-2,6-dioxo-3,5-piperidinedicarboxylate 
• 459-57-4 4-fluorobenzaldehyde 
• 420808-42-0 dimethyl 2-(4-fluorophenyl)-4-hydroxy-4-methyl-6-oxocyclohexane-1,3-dicarboxylate 
• 3449-63-6 3-(4-fluorophenyl)pentan-1,5-dioic acid 
• 52927-40-9 dimethyl 2-(4-fluorobenzylidene)malonate 
• 76311-95-0 methyl 3-(methylamino)-3-oxopropanoate 

Relevant academic research and scientific papers

A novel chiral base mediated glutarimide desymmetrisation: Application to the asymmetric synthesis of (-)-paroxetine

The asymmetric desymmetrisation of certain 4-aryl substituted glutarimides has been accomplished with high levels of selectivity (up to 97% ee) by enolisation with a chiral bis-lithium amide base. The selectivity of the reaction is shown to be the result of asymmetric enolisation, followed by a kinetic resolution. One of the chiral imides synthesised was converted into the selective seratonin reuptake inhibitor (-)-paroxetine.

COMPOUNDS AND PROCESS TO PREPARE CHIRAL INTERMEDIATES FOR SYNTHESIS OF PAROXETINE

Provided herein are compounds and processes that produce intermediates and precursors of paroxetine and related compounds. Also provided are processes for the preparation of paroxetine.

Application of the chiral base desymmetrisation of imides to the synthesis of the alkaloid jamtine and the antidepressant paroxetine

The synthesis of the alkaloid jamtine and the antidepressant paroxetine have been addressed by a strategy involving asymmetric desymmetrisation of prochiral imides by a chiral lithium amide base. A short reaction sequence, starting with a cyclohexane fused succinimide, led to the structures originally reported for the alkaloid jamtine and its derived N-oxide. The structures synthesised are shown not to correspond with those originally reported. A second sequence involves desymmetrisation of a 4-arylglutarimide, and provides a short enantioselective synthesis of the drug substance paroxetine.