7724-28-9

Upstream product

• 874005-61-5 2,5-diethoxy-tetrahydro-furan-3-ol 
• 3675-13-6 cis-butenedial 
• 332-77-4 2,5-dihydro-2,5-dimethoxyfuran 
• 131543-46-9 Glyoxal 
• 75-07-0 acetaldehyde 

Downstream Products

• 42890-76-6 (S)-1,2,4-butanetriol 

Relevant academic research and scientific papers

Synthesis of the 2β,3β-, 2α,3β-, 2β,3α- and 2α,3α-isomers of 6β-hydroxy-3-(p-tolyl)tropane-2-carboxylic acid methyl ester

6-Hydroxytropanone (8) was synthesized by a Mannich type condensation between acetonedicarboxylic acid, methylamine hydrochloride, and the hydrolysis product of 2,5-dimethoxydihydrofuran and was used as the key intermediate for the synthesis of the four r

Second-Generation palladium catalyst system for transannular C-H functionalization of azabicycloalkanes

This article describes the development of a second-generation catalyst system for the transannular C-H functionalization of alicyclic amines. Pyridine- and quinoline-carboxylate ligands are shown to be highly effective for increasing the reaction rate, yield, and scope of Pd-catalyzed transannular C-H arylation reactions of azabicyclo[3.1.0]hexane, azabicyclo[3.1.1]heptane, azabicyclo[3.2.1]octane, and piperidine derivatives. Mechanistic studies reveal that the pyridine/quinoline-carboxylates play a role in impeding both reversible and irreversible catalyst decomposition pathways. These ligands enable the first reported examples of the transannular C-H arylation of the ubiquitous tropane, 7-azanorbornane, and homotropane cores. Finally, the pyridine/quinoline-carboxylates are shown to promote both transannular C-H arylation and transannular C-H dehydrogenation on a homotropane substrate.

Total Synthesis of (±)-Scopolamine: Challenges of the Tropane Ring

Scopolamine was synthesized using 6,7-dehydrotropine as a key intermediate. Rhodium-catalyzed [4 + 3] cycloaddition chemistry and a modified Robinson-Sch?pf reaction were each independently evaluated for their utility in constructing the tropane core. Both synthetic approaches gave comparable overall yields.

Asymmetric aldol reaction of glyoxal catalyzed by diarylprolinol

All selection should be this- eeasy: The direct asymmetric aldol reaction of commercial aqueous glyoxal is catalyzed by trifluoromethyl-substituted diarylprolinol 1 to afford a β-formyl-β-hydroxy-α-substituted aldehyde in good yield with excellent anti selectivity and excellent enantioselectivity.

Syntheses of (-)-pelletierine and (-)-homopipecolic acid

Enantiomeric syntheses of (-)-homopipecolic acid and (-)-pelletierine have been achieved by chiral resolution of tropanol followed by Baeyer-Villiger oxidation. The methodology provides a practical route for the synthesis of optically pure piperidines. The Royal Society of Chemistry 2012.

Enzymatic Resolution of Tropinone Derivatives

The lipase-mediated kinetic resolution of racemic scopoline [(±)-4] and 6-hydroxytropinone [(±)-7] is reported. Whereas (±)-4 is difficult to resolve due to steric hindrance of the hydroxy function, the resolution of (±)-7 with vinyl acetate as acyl donor gave alcohol (+)-7 and the corresponding acetate (-)-9 with high enantiomeric excess. In case of the optimal result of 99% ee for (+)-7 and 80% ee for (-)-9, an E-value of 35 was calculated. The preparative lipase-catalyzed resolution of (±)-7 resulted in almost enantiopure alcohol (+)-7 with >99% ee after one recrystallization.

Chemical synthesis and pharmacology of 6- and 7-hydroxylated 2-carbomethoxy-3-(p-tolyl)tropanes: Antagonism of cocaine's locomotor stimulant effects

In our efforts to identify molecules that might act as cocaine antagonists or cocaine partial agonists, efforts were made to further capitalize on our earlier finding regarding the ability of a 7-methoxylated pseudococaine analogue to act as a weak cocain

Synthesis of 6- or 7- hydroxy and 6- or 7- methoxy tropanes

A novel Mannich type condensation between the monomethyl ester of acetonedicarboxylic acid, methylamine hydrochloride, and hydrolyzed dimethoxydihydrofuran gave 6- or 7- functionalized β-keto ester tropanes 12 - 15. Further elaboration afforded a series of 6- or 7- hydroxy and 6- or 7-methoxy 2β-methoxycarbonyl-3-aryltropanes.