230642-83-8

Upstream product

• 312490-77-0 C₂₄H₂₆O₇S₂ 
• 199391-75-8 2,3-bis(2-hydroxyethyl)phenol 
• 98-59-9 p-toluenesulfonyl chloride 
• 36192-01-5 5,8-dihydro-1-naphthyl benzyl ether 
• 27673-48-9 5,8-dihydro-1-naphthol 

Downstream Products

• 230642-84-9 4-ethenyl-2,3-dihydro-1-benzofuran 
• 209257-15-8 trans-[2-(2,3-dihydro-4-benzofuranyl)cyclopropyl]methanamine 
• 209257-15-8 1-[(1R,2R)-2-(2,3-dihydro-1-benzofuran-4-yl)cyclopropyl]methanamine 
• 609799-22-6 [14C]-Tasimelteon 

Relevant academic research and scientific papers

Tasimelteon intermediate and preparation method thereof

The invention provides a tasimelteon intermediate and a preparation method thereof. The preparation method comprises the following steps: with a compound a as a raw material, reacting the compound a with benzyl bromide so as to obtain a compound I; then subjecting the compound I to a reaction under the action of a combined catalyst consisting of potassium osmate dihydrate, potassium carbonate, potassium ferricyanide, benzyltriethylammonium chloride and methane sulfonamide or a combined catalyst consisting of osmium tetroxide, potassium carbonate, potassium ferricyanide, benzyltriethylammonium chloride and methane sulfonamide so as to obtain a compound II; subjecting the compound II to an oxidation reaction under the action of sodium periodate or lead tetraacetate so as to obtain an intermediate compound III and carrying out a reduction reaction so as to obtain a compound IV; and subjecting the compound IV to a reduction reaction to remove a benzyl protective group so as to obtain a compound V, then reacting the compound V with p-toluene sulfonyl chloride, carrying out hydroxyl protection and then carrying out cyclization under the action of potassium carbonate so as to obtain the tasimelteon intermediate compound VI. The invention provides a novel process for preparation of the tasimelteon intermediate; and the prepared tasimelteon intermediate has good purity and high quality and is applicable to industrial production.

A facile and practical synthesis of (-)-tasimelteon

An efficient and practical route for the synthesis of (-)-tasimelteon from 2,3-bis(2-hydroxyethyl)phenol has been developed. The product was prepared in seven steps in overall 16.4% yield using highly stereoselective cyclopropanation reaction of the intermediate as the key step.

ACYL GUANIDINE SODIUM/PROTON EXCHANGE INHIBITORS AND METHOD

Acyl guanidines are provided which are sodium/proton exchange (NHE) inhibitors which have the structure wherein n is 1 to 5; X is N or C-R5 wherein R5 is H, halo, alkenyl, alkynyl, alkoxy, alkyl, aryl or heteroaryl; and R1, R2, R3 and R4 are as defined herein, and where X is N, R1 is preferably aryl or heteroaryl, and are useful as antianginal and cardioprotective agents. In addition, a method is provided for preventing or treating angina pectoris, cardiac dysfunction, myocardial necrosis, and arrhythmia employing the above acyl guanidines.