87250-97-3

Basic information

• Product Name: tert-butyl 3-oxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-carboxylate
• Synonyms: tert-butyl 3-oxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-carboxylate
• CAS NO: 87250-97-3
• Molecular Weight: 213.233
• Mol File: 87250-97-3.mol
• Article Data: 19

Chemical Properties

• CAS DataBase Reference: tert-butyl 3-oxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl 3-oxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-carboxylate(87250-97-3)
• EPA Substance Registry System: tert-butyl 3-oxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-carboxylate(87250-97-3)

Safety Data

• Hazardous Substances Data: 87250-97-3(Hazardous Substances Data)

Upstream product

• 1972-28-7 diethylazodicarboxylate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 51-35-4 4R-4-hydroxyproline 
• 1332341-02-2 benzyl (2S)-2-Boc-amino-3-(2-oxiranyl)propionate 
• 74844-91-0 1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate 
• 202477-59-6 (2S,4R)-1-(tert-butoxycarbonyl)-4-[(methylsulfonyl)oxy]-2-pyrrolidinecarboxylic acid 
• 13726-69-7 (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid 

Downstream Products

• 87691-28-9 cis-N-tert-butoxycarbonyl-4-hydroxy-L-prolylglycine benzyl ester 
• 74844-91-0 (2S,4S)-N-tert-butoxycarbonyl-4-hydroxyproline methyl ester 
• 87691-27-8 N-tert-butoxycarbonyl-L-cis-4-hydroxyproline 
• 1434818-13-9 benzenesulfonic acid (3S,5S)-5-(1-cyano-cyclopropylcarbamoyl)-1-(1-trifluoromethylcyclopropanecarbonyl)-pyrrolidin-3-yl ester 
• 1434818-32-2 benzenesulfonic acid (3S,5S)-5-(1-cyanocyclopropylcarbamoyl)-1-(1-methylcyclopropanecarbonyl)pyrrolidin-3-yl ester 
• 1447448-21-6 C₂₉H₄₄N₄O₈SSi 
• 1252634-14-2 (2S,4R)-4-[2-chloro-4-((S)-2,2,2-trifluoro-1-methylethoxy)benzenesulfonyl]-1-(1-trifluoromethylcyclopropanecarbonyl)pyrrolidine-2-carboxylic acid (1-cyano-cyclopropyl)amide 

Relevant articles and documents

cis-4-Alkoxydialkyl- and cis-4-Alkoxydiarylprolinol Organocatalysts: High Throughput Experimentation (HTE)-Based and Design of Experiments (DoE)-Guided Development of a Highly Enantioselective aza-Michael Addition of Cyclic Imides to α,β-Unsaturated Aldehydes

A diverse family (37 compounds) of cis-4-alkoxydiorganylprolinol derivatives has been prepared and evaluated in organocatalysis for the first time. The combined use of high throughput experimentation (HTE) techniques with efficient analytical methods has led to the identification of two superior catalysts for the enantioselective addition of succinimide to α,β-unsaturated aldehydes. Further optimization of the reaction conditions with design of experiments (DoE) techniques established the catalyst of choice for the considered aza-Michael reaction, the corresponding adducts (12 examples) being obtained in good yields and excellent enantioselectivities (succinimide and maleimide donors). The synthetic versatility of these Michael adducts is illustrated by a two-step sequence leading to enantiopure 1,3-amino alcohols. (Figure presented.).

Automated Radiosynthesis of cis- And trans-4-[18F]Fluoro- l -proline Using [18F]Fluoride

The positron emission tomography imaging agents cis- and trans-4-[18F]fluoro-l-proline are used for the detection of numerous diseases such as pulmonary fibrosis and various carcinomas. These imaging agents are typically prepared by nucleophilic fluorination of 4-hydroxy-l-proline derivatives, with [18F]fluoride, followed by deprotection. Although effective radiofluorination reactions have been developed, the overall radiosynthesis process is suboptimal due to deprotection methods that are performed manually, require multiple steps, or involve harsh conditions. Here we describe the development of two synthetic routes that allow access to precursors, which undergo highly selective radiofluorination reactions and rapid deprotection, under mild acidic conditions. These methods were found to be compatible with automation, avoiding manual handling of radioactive intermediates.

Synthesis of (1R,4R)-2,5-diazabicyclo[2.2.1]heptane derivatives by an epimerization-lactamization cascade reaction

An epimerization-lactamization cascade of functionalized (2S,4R)-4-aminoproline methyl esters is developed and applied in synthesizing (1R,4R)-2,5-diazabicyclo[2.2.1]heptane (DBH) derivatives. (2S,4R)-4-Aminoproline methyl esters are likely to undergo 2-epimerization under basic conditions, followed by an intramolecular aminolysis of the (2R)-epimer to form the bridged lactam intermediates. Key factors identified for this cascade reaction include the electron-withdrawal N-protective group in the substrates and a strong base as the promoter.