72485-25-7

Usage

Uses

Used in Pharmaceutical Industry:
2-Oxa-5-azabicyclo[2.2.1]heptan-3-one, 5-acetyl-, (1S)(9CI) is used as a key intermediate in the synthesis of various pharmaceutical compounds due to its unique bicyclic structure and functional groups. Its reactivity and chirality allow for the development of enantioselective reactions, leading to the production of chiral drugs with improved efficacy and reduced side effects.
Used in Organic Synthesis:
In the field of organic synthesis, 2-Oxa-5-azabicyclo[2.2.1]heptan-3-one, 5-acetyl-, (1S)(9CI) serves as a versatile building block for the creation of complex organic molecules. Its acetate functional group can be further modified through various chemical reactions, enabling the synthesis of a wide range of compounds with diverse applications, such as agrochemicals, fragrances, and dyes.
Used in Research and Development:
2-Oxa-5-azabicyclo[2.2.1]heptan-3-one, 5-acetyl-, (1S)(9CI) is utilized in research and development for studying the properties and reactivity of bicyclic lactams. Its unique structure provides opportunities for exploring new reaction pathways and developing innovative synthetic methods, contributing to the advancement of organic chemistry and related fields.

Upstream product

• 100895-61-2 N-acetyl-trans-4-(tosyloxy)-L-proline 
• 108-24-7 acetic anhydride 
• 3398-22-9 trans-4-hydroxyproline 
• 57750-51-3 (3R,5S)-5-(methoxycarbonyl)-1-acetylpyrrolidin-3-yl 4-methylbenzenesulfonate 
• 67943-19-5 methyl (2S,4R)-1-acetyl-4-hydroxypyrrolidine-2-carboxylate 
• 33996-33-7 oxaceprol 

Downstream Products

• 78804-96-3 (2S,4S)-1-acetyl-4-hydroxyproline methyl ester 
• 109492-70-8 (2S,4S)-1-acetyl-4-hydroxyproline ethyl ester 

Relevant academic research and scientific papers

Synthesis of a histamine H3 receptor antagonist - Manipulation of hydroxyproline stereochemistry, desymmetrization of homopiperazine, and nonextractive sodium triacetoxyborohydride reaction workup

(Figure presented) We have recently completed the synthesis of 1-[2-(4-cyclobutyl-[1,4]diazepane-1-carbonyl)-4-(3-fluoro-phenoxy) -pyrrolidin-1-yl]-ethanone, a hydroxyproline-based H3 receptor antagonist, on 100 g scale. The synthesis proceeds through four steps and route selection was driven by a desire to minimize the cost-of-goods. Naturally occurring trans-4-hydroxy-L-proline was chosen as the precursor to the targets core, which necessitated an inversion at both stereogenic centers. The inversions were accomplished through strategic employment of La Rosas lactone and a late-stage Mitsunobu reaction. A first generation synthesis that employed N-Boc-homopiperazine was improved in a second generation approach wherein homopiperazine was directly desymmetrized. Finally, the water solubility of a key intermediate necessitated the development of a nonextractive workup for the sodium triacetoxyborohydride reduction.

Synthetic Applications of Electrochemically Produced α-Methoxyamides. Part 2) Oxidation of Hydroxyproline Derivatives

The electrochemical methoxylation of N-acetyl-4-hydroxyproline esters has been investigated.Both the free alcohol 3 and the corresponding 4-acetoxy derivative 4 as well as the cis-4-acetoxyproline 17 are methoxylated anodically preferentially at C(5), giving a mixture of stereoisomeric methoxy compounds.These mixtures can be used for further substitution as exemplified by the allylation of the methoxylated 4-acetoxy derivatives, giving substitution products preferentially trans to the acetoxy group although with low selectivity.The low selectivity is discussed in terms of kinetic vs. thermodynamic control.

A SHORT IMPROVED SYSTHESIS OF N-SUBSTITUTED 5-AZA-2-OXA-3-OXO-BICYCLOHEPTANES

N-Substituted 5-aza-2-oxa-3-oxo-bicycloheptanes are conformationally rigid models that have been used in several 1H-NMR studies.They have previously been obtained by multistep processes.We have devised a one step synthesis for these compounds.The utility of this new route has been demonstrated for five differently N-substituted substrates.