419563-22-7

Usage

Uses

Used in Pharmaceutical Industry:
(1R,4S)-Methyl 4-aMinocyclopent-2-enecarboxyla is used as an intermediate in the synthesis of peramivir (P285500), a neuraminidase inhibitor. The application reason for this use is that peramivir is an antiviral agent specifically developed for the treatment of influenza. By inhibiting the neuraminidase enzyme, peramivir prevents the replication and spread of the influenza virus, thus providing relief from the symptoms and shortening the duration of the illness.

Upstream product

• 426226-35-9 (1S*,4R*)-4-amino-2-cyclopentene-1-carboxylic acid methyl ester hydrochloride 
• 87-69-4 L-Tartaric acid 
• 67-56-1 methanol 
• 49805-30-3 racemic 2-azabicyclo[2.2.1]hept-5-en-3-one 
• 49805-30-3 2-azabicyclo[2.2.1.]hept-5-en-3-one 
• 147-71-7 D-tartaric acid 

Downstream Products

• 168683-02-1 (1S,4R)-(-)-methyl-[[(1,1-dimethylethoxy)carbonyl]amino]cyclopent-2-ene-1-carboxylate 
• 168960-18-7 (1R,4S)-N-(tert-Butyloxycarbonyl)-1-amino-4-(hydroxymethyl)-2-cyclopentene 
• 251326-99-5 (1R,4S)-N-tert-butoxycarbonyl-4-aminocyclopent-2-ene-1-carboxylic acid methyl ester 
• 153011-43-9 (1S,cis)-tert-butyl N-[4-(hydroxymethyl)-2-cyclopenten-1-yl]carbamate 
• 168960-19-8 (1R,4S)-1-amino-4-(hydroxymethyl)-2-cyclopentene hydrochloride 
• 229613-93-8 (+)-methyl (3aR,4R,6S,6aS)-4-[(tert-butoxycarbonyl)-amino]-3-(1-ethylpropyl)-4,5,6,6a-tetrahydro-3aH-cyclopenta[d]isoxazole-6-carboxylate 

Relevant academic research and scientific papers

Chemical preparation method of 2-azabicyclo [2.2.1] hept-5-ene-3-one with optical activity

The invention discloses a chemical preparation method of 2-azabicyclo [2.2.1] hept-5-ene-3-one with optical activity. The chemical preparation method comprises the following steps: racemic 2-azabicyclo [2.2.1] hept-5-ene-3-one which is easily available on the market is used as a raw material and is subjected to chemical resolution to obtain (+/-) 4-aminocyclopent-2-ene-1-carboxylic acid methyl ester with optical activity, (+/-) 4-aminocyclopent-2-ene-1-carboxylic acid is prepared by hydrolysis, and the (+/-) 4-aminocyclopent-2-ene-1-carboxylic acid is subjected to intramolecular condensation to obtain the 2-azabicyclo [2.2.1] hept-5-ene-3-one with optical activity. The method has the advantages that the use of an enzyme fermentation method is avoided, the repeatability is good, and the yield is high.

Optical pure amino alcohol hydrochloride preparation method

The invention relates to a preparation method for optically pure aminoalcohol hydrochloride. The optically pure aminoalcohol hydrochloride is any one selected from optically pure aminoalcohol hydrochloride 1 and optically pure aminoalcohol hydrochloride 2 and is prepared by subjecting a compound 4 to an esterification ring-opening reaction, an amino protection reaction, an ester reduction reaction and a deprotection salt forming reaction. The optically pure aminoalcohol hydrochloride 1 or optically pure aminoalcohol hydrochloride 2 prepared in the invention can be directly used for synthesis of abacavir and carbovir. The preparation method provided by the invention has the advantages of high product optical purity, stable product quality, high product yield, a small amount of environmental pollution, low production cost, easy industrialization, etc.

PROCESS FOR THE PREPARATION OF AMINO ALCOHOL DERIVATIVES OR SALTS THEREOF

The present invention relates to a process for the preparation of amino alcohol derivatives or salts thereof. In particular the present invention relates to process for the preparation of amino alcohol derivatives or salts thereof which may be used as intermediates in the preparation of HIV reverse transcriptase inhibitors, more preferably Carbovir and Abacavir. The present invention more specifically relates to a process for the preparation of (1S,4R)-4-amino-2-cyclopentene-1-methanol of Formula IIIa. The present invention also specifically relates to process for the preparation of Abacavir sulfate of Formula II using compound of Formula IIIa prepared according to the process of the present invention.

PRODUCTION METHOD FOR CIS-1-AMINO-4-HYDROXYMETHYL-2-CYCLOPENTENE OR ITS SALT

PROBLEM TO BE SOLVED: To provide a method capable of producing cis-1-amino-4-hydroxymethyl-2-cyclopentene or its salt with high selectivity and a high yield by using inexpensive reactants easily handleable. SOLUTION: Cis-1-amino-4-hydroxymethyl-2-cyclopentene represented by formula (II) or its salt is produced by mixing a cis-4-amino-2-cyclopentene-1-carboxylic ester salt represented by general formula (I) (wherein R1 is an optionally substituted alkyl, cycloalkyl, alkenyl, alkynyl, aryl, or aralkyl group; and A is an inorganic or organic acid residue) with a metal boron hydride complex compound under the condition that the stoichiometric ratio of the amount of the metal boron hydride complex compound to the amount of the cis-4-amino-2-cyclopentene-1-carboxylic ester salt is 1-10. COPYRIGHT: (C)2006,JPOandNCIPI

Process for preparing (-)-(1S, 4R) N-protected 4-amino-2-cyclopentene-1-carboxylate esters

The invention relates to a process for preparing (?)-(1S,4R) N protected 4-amino-2-cylcopentene-1-carboxylate esters represented by the formula (I) wherein R1 and R2 are as described within the specification.