1400898-49-8

Basic information

• Product Name: ((1R,2R)-2-(2,3-dihydrobenzofuran-4-yl)cyclopropyl)methanamine
• Synonyms: ((1R,2R)-2-(2,3-dihydrobenzofuran-4-yl)cyclopropyl)methanamine;((1R,2R)-2-(2,3-dihydrobenzofuran-4-yl)cyclopropyl)methanamine((1R,2R)-2-(2,3-dihydrobenzofuran-4-yl)cyclopropyl)methanamine
• CAS NO: 1400898-49-8
• Molecular Formula: C12H15NO
• Molecular Weight: 189.2536
• Mol File: 1400898-49-8.mol
• Article Data: 11

Chemical Properties

• Appearance: /
• CAS DataBase Reference: ((1R,2R)-2-(2,3-dihydrobenzofuran-4-yl)cyclopropyl)methanamine(CAS DataBase Reference)
• NIST Chemistry Reference: ((1R,2R)-2-(2,3-dihydrobenzofuran-4-yl)cyclopropyl)methanamine(1400898-49-8)
• EPA Substance Registry System: ((1R,2R)-2-(2,3-dihydrobenzofuran-4-yl)cyclopropyl)methanamine(1400898-49-8)

Safety Data

• Hazardous Substances Data: 1400898-49-8(Hazardous Substances Data)

Usage

Uses

((1R,2R)-2-(2,3-Dihydrobenzofuran-4-yl)cyclopropyl)methanamine is an intermediate int he synthesis of Tasimelteon (T007740), a novel drug, used in the treatment of non-24 hour sleep-wake disorder. It helps to correct the circadian rhythm disorder often seen in patients who are visually impaired.

Upstream product

• 199391-75-8 2,3-bis(2-hydroxyethyl)phenol 
• 230642-83-8 C₁₇H₁₈O₄S 
• 230642-84-9 4-ethenyl-2,3-dihydro-1-benzofuran 
• 209256-40-6 2,3-dihydrobenzofuran-4-carboxylic acid 
• 209256-81-5 (trans)-N-methoxy-N-methyl-3-(2,3-dihydrobenzofuran-4-yl)propenamide 
• 166599-84-4 benzofuran-4-carboxylic acid 
• 209256-42-8 2,3-dihydro-1-benzofuran-4-carbaldehyde 
• 209256-41-7 (2,3-dihydro-benzofuran-4-yl)-methanol 
• 209256-69-9 (2E)-3-(2,3-dihydro-1-benzofuran-4-yl)prop-2-enoic acid 
• 219581-93-8 3-(2,3-dihydrobenzofuran-4-yl)-2-propenoyl chloride 
• 30595-79-0 2-(2,6-dichlorophenyl)ethan-1-ol 

Relevant articles and documents

An efficient and practical asymmetric synthesis of (?)-tasimelteon

Tasimelteon is a useful drug for the treatment of Non-24 in totally blind individuals. An efficient and convenient asymmetric synthesis of tasimelteon has been developed from 4-vinyl-2,3-dihydrobenzofuran through six steps in 53% overall yield using the Corey–Bakshi–Shibata (CBS0 asymmetric reduction of ketone as a key step.

Total synthesis of Tasimelteon

A simple and efficient approach has been accomplished for the total synthesis of active pharmaceutical ingredient (API) of Tasimelteon which is effective for treatment of non-24-h sleep-wake disorder. Starting from 4-vinyl-2, 3-dihydrobenzofuran, the synthesis involves asymmetric epoxidation, Wittig reaction, reduction of the nitrile group and propionation of the amine. The synthesis was accomplished in four steps in overall 48% yield.

PROCESS FOR THE PREPARATION OF ENANTIOMERICALLY ENRICHED DIHYDROBENZOFURANS AND INTERMEDIATE COMPOUNDS OBTAINED IN THE PROCESS

It is described an industrially viable and advantageous process for the preparation of (N- (((1R,2R)-2-(2,3-dihydrobenzofuran-4-yl)cyclopropyl)methyl)propionamide, compound having the formula depicted below and generally known as Tasimelteon, or of intermediates useful in the synthesis thereof: The invention also relates to salts obtained as intermediates of the process.