916069-80-2

Usage

Uses

Used in Organic Synthesis:
(S)-4-(Fluoromethyl)-dihydrofuran-2(3H)-one is used as a key intermediate in organic synthesis for the preparation of various organic compounds. Its distinctive structure allows for the creation of a wide range of molecules with diverse applications.
Used in Pharmaceutical Research:
In the pharmaceutical industry, (S)-4-(Fluoromethyl)-dihydrofuran-2(3H)-one serves as a crucial building block for the development of new drugs. Its unique properties make it an attractive candidate for the design and synthesis of novel therapeutic agents.

Upstream product

• 916069-73-3 3-tert-butoxymethyl-4-fluoro-3-hydroxybutyric acid tert-butyl ester 
• 916069-74-4 4-fluoromethyl-4-hydroxy-dihydro-furan-2-one 
• 1333377-20-0 C₁₃H₂₅FO₃ 
• 1333379-12-6 C₇H₉ClO₄ 
• 1333379-20-6 C₅H₇ClO₂ 
• 1333378-95-2 C₉H₁₆O₄ 
• 80904-75-2 4-hydroxymethyl-5H-furan-2-one 
• 127181-22-0 (1R,5S)-methyl 2-oxo-3-oxabicyclo[3.1.0]hexane-1-carboxylate 
• 201804-32-2 tert-butyl 4-hydroxy-3-(hydroxymethyl)butanoate 
• 192214-01-0 Toluene-4-sulfonic acid (S)-5-oxo-tetrahydro-furan-3-ylmethyl ester 
• 85701-08-2 (R)-4-(hydroxymethyl)dihydrofuran-2(3H)-one 
• 1021943-70-3 C₁₂H₂₁FO₅ 
• 916069-77-7 4-fluoromethyl-5H-furan-2-one 

Relevant academic research and scientific papers

Development of a scalable synthesis of (S)-3-fluoromethyl-γ- butyrolactone, building block for Carmegliptin's Lactam moiety

Several new routes are reported for the synthesis of (S)-3-fluoromethyl- γ-butyrolactone. An asymmetric hydrogenation-based synthesis was chosen as the enabling route to produce the lactone on a 10-kg scale. A superior stereoselective route starting from (S)-tert-butyl glycidyl ether which afforded the desired lactone in three steps with ～50% overall yield was finally selected for further development and production.

Discovery of carmegliptin: A potent and long-acting dipeptidyl peptidase IV inhibitor for the treatment of type 2 diabetes

Design, synthesis, and SAR are described for a class of DPP-IV inhibitors based on aminobenzo[a]quinolizines with non-aromatic substituents in the S1 specificity pocket. One representative thereof, carmegliptin (8p), was chosen for clinical development. Its X-ray structure in complex with the enzyme and early efficacy data in animal models of type 2 diabetes are also presented.

PROCESS FOR THE PREPARATION OF (S)-4-FLUOROMETHYL-DIHYDRO-FURAN-2-ONE

The present invention relates to a process of the preparation of (S)-4-fluoromethyl-dihydro-furan-2-one of the formula by employing a dialkylmalonate of the formula wherein R1b is lower alkyl, and the use of this process for the manufacture of DPP-IV inhibitors that are useful for the treatment and/or prophylaxis of diseases such as diabetes.

PROCESS FOR THE PREPARATION OF PYRIDO [2,1-a] ISOQUINOLINE DERIVATIVES COMPRISING OPTICAL RESOLUTION OF AN ENAMINE

This invention relates to a process for the preparation of pyrido[2,1-a]isoquinoline derivatives of the formula wherein R1, R2, R3 and R4 are defined in the specification, comprising the optical resolution of an

PROCESS FOR THE PREPARATION OF PYRIDO [ 2-1-A] ISOQUINOLINE DERIVATIVES BY CATALYTIC ASYMMETRIC HYDROGENATION OF AN ENAMINE

The invention relates to a process for the preparation of pyrido[2,1-a] isoquinoline derivatives of the formula wherein R2, R3and R4 are as defined in the specification, comprising the steps of a) catalytic asymmetric hydr

Process for the preparation of (S)-4-fluoromethyl-dihydro-furan-2-one useful in the preparation of the DPP-IV inhibitor (S)-1 ((2S,3S,11bS)-2-amino-9,10-dimethoxy-1,3,4,6,7, 11b-hexahydro-2h-pyrido[2,1-a] isoquinolin-3-yl)-4-fluoromethyl-pyrrolidin-2-one

This invention relates to a process of the preparation of the novel intermediate (S)-4-fluoromethyl-dihydro-furan-2-one of the formula and with its use for the manufacture of pyrido[2,1-a]isoquinoline derivatives of the formula which are useful for the treatment and/or prophylaxis of diseases which are associated with DPP IV.