1243634-65-2

Upstream product

• 79-20-9 acetic acid methyl ester 
• 1355075-44-3 (S)-(+)-3-(2-propyl-1,3-dioxolan-2-yl)propylidene-p-toluenesulfinamide 
• 105-21-5 4-propylbutanolide 
• 41221-88-9 3-(2-propyl-1,3-dioxolan-2-yl)propanal 
• 1360562-59-9 4-hydroxy-N-methoxy-N-methylheptanamide 
• 1360562-65-7 N-methoxy-N-methyl-3-(2-propyl-1,3-dioxolan-2-yl)propanamide 
• 188447-91-8 (S)-p-toluenesulfinimide 

Downstream Products

• 1243634-66-3 (S(S),3S)-(+)-N-(p-toluenesulfinyl)-3-amino-5-(2-propyl-1,3-dioxolan-2-yl)pentanal 

Relevant academic research and scientific papers

COCAINE ANALOGS AND METHODS OF PREPARATION AND USES THEREOF

The invention provides novel cocaine analogs. The invention also provides a method of preparing cocaine analogs with control over the substituents installed at the C-1, C-2, C-3, C-4 and N-8 positions of the tropane bicyclic scaffold. The invention further provides a method of providing anesthesia to a subject in need thereof comprising administering to the subject a pharmaceutical composition comprising a compound of the invention. The invention also provides a method of blocking reuptake of a monoamine neurotransmitter in a subject in need thereof, to a subject in need thereof comprising administering to the subject a pharmaceutical composition comprising a compound of the invention.

Enantioselective synthesis of cocaine C-1 analogues using sulfinimines (N -sulfinyl imines)

The first examples of cocaine analogues having substituents (methyl, ethyl, n-propyl, n-pentyl, and phenyl) at the C-1 position of the cocaine tropane skeleton were prepared by heating sulfinimine-derived α,β-unsaturated pyrrolidine nitrones. In the presence of the Lewis acid Al(O tBu)3 the nitrones undergo an intramolecular [3 + 2] cycloaddition to give tricyclic isoxazolidines that were transformed in three steps to the cocaine analogues. In the absence of the Lewis acid, lactams were formed resulting from rearrangement of the nitrone to an oxaziridine. A novel Pd- and base-promoted rearrangement of methanesulfonate salts of isoxazolidine to bridge bicyclic[4.2.1]isoxazolidines was discovered.

Asymmetric total synthesis of (S)-(+)-cocaine and the first synthesis of cocaine C-1 analogs from N -sulfinyl β-amino ester ketals

Sulfinimine-derived α,β-unsaturated pyrrolidine nitrones, on heating with Al(O-t-Bu)3, undergo a highly stereoselective intramolecular [3 + 2] cycloaddition to give tricyclic isoxazolidines, which are transformed in three-steps to give C-1 substituted cocaine analogs.