109431-87-0

Usage

Uses

Used in Pharmaceutical Industry:
(R)-(-)-N-Boc-3-pyrrolidinol is used as a key intermediate in the synthesis of various pharmaceuticals, including antibiotics, antidepressants, and antipsychotics. Its chiral nature allows for the selective synthesis of enantiomerically pure compounds, which is crucial for the development of drugs with improved efficacy and reduced side effects.
Used in Agrochemical Industry:
(R)-(-)-N-Boc-3-pyrrolidinol is also used as a precursor in the synthesis of agrochemicals, such as insecticides and herbicides. Its ability to form stable derivatives with other molecules makes it a valuable component in the development of new and effective crop protection agents.
Used in Synthesis of Ligands for the Nicotinic Acetylcholine Receptor:
(R)-(-)-N-Boc-3-pyrrolidinol is used as a building block in the synthesis of ligands for the nicotinic acetylcholine receptor. These ligands are important for the study of the receptor's function and for the development of drugs targeting this receptor, which is involved in various neurological disorders, such as Alzheimer's disease and schizophrenia.
Chemical Properties:
(R)-(-)-N-Boc-3-pyrrolidinol is a white to off-white powder with a molecular weight of 173.24 g/mol. It is soluble in common organic solvents, such as dichloromethane, ethyl acetate, and acetone, and has a melting point of around 65-68°C. Its chemical stability and reactivity make it a versatile compound for various synthetic applications.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 101469-91-4 (3S)-1-benzyl-3-hydroxypyrrolidine-2,5-dione 
• 104706-47-0 (R)-3-hydroxypyrrolidine hydrochloride 
• 123-91-1 1,4-dioxane 
• 101385-93-7 3-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 101469-92-5 (S)-3-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 132945-75-6 (S)-tert-butyl 3-(methylsulfonyloxy)pyrrolidine-1-carboxylate 
• 101408-94-0 3R-acetoxypyrrolidine-1-carboxylic acid tert-butyl ester 
• 101385-90-4 (R)-N-benzyl-3-hydroxypyrrolidine 
• 40499-83-0 (3R)-pyrrolidinol 
• 1070-19-5 N-(tert-butyloxycarbonyl) azide 
• 51-35-4 4R-4-hydroxyproline 
• 549532-09-4 3R-(tert-butyl-dimethylsilyloxy)pyrrolidine-1-carboxylic acid tert-butyl ester 

Downstream Products

• 150613-54-0 4-<<(3S)-1-(tert-butoxycarbonyl)-3-pyrrolidinyl>oxy>benzaldehyde 
• 139986-03-1 1,1-dimethylethyl-3(R)-{[(4-methylphenyl)sulphonyl]oxy}-1-pyrrolidinecarboxylate 
• 114676-93-6 (2R,4R)-tert-butyl 4-hydroxy-2-methylpyrrolidine-1-carboxylate 
• 114676-61-8 tert-butyl (2S,4R)-4-hydroxyl-2-methylpyrrolidine-1-carboxylate 
• 188576-54-7 7-<<4-(1-(tert-butoxycarbonyl)pyrrolidin-3(S)-yloxy)phenyl>(ethoxycarbonyl)methoxy>-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester 
• 132945-74-5 (S)-N-tert-butoxycarbonylpyrrolidin-3-yl benzoate 
• 101408-94-0 3R-acetoxypyrrolidine-1-carboxylic acid tert-butyl ester 
• 549532-08-3 3R-methoxypyrrolidine-1-carboxylic acid tert-butyl ester 
• 150610-51-8 diethyl 2-(4-{[(3S)-1-(tert-butoxycarbonyl)pyrrolidin-3-yl]oxy}phenyl)malonate 
• 741290-77-7 tert-butyl (3S)-3-(3-nitrophenoxy)pyrrolidine-1-carboxylate 
• 127342-35-2 3-(2-methoxy-phenoxy)-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 479253-00-4 tert-butyl (S)-3-fluoropyrrolidine-1-carboxylate 
• 101385-93-7 3-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 150610-38-1 ethyl 2-<4-<<(3S)-1-(tert-butoxycarbonyl)-3-pyrrolidinyl>oxy>phenyl>-2-oxoacetate 

Relevant academic research and scientific papers

Enantiospecific Synthesis of the (4R)-1-Azabicycloheptane Ring System

An enantioselective synthesis of (4R)-1-azabicycloheptane derivatives is described commencing from readily available trans-4-hydroxy-L-proline which is converted into the key intermediate (3R)-N-(tert-butoxycarbonyl)-3-methylsulfonyloxypyrrolidine 4.Reaction of the sulfonate ester 4 with an enolate anion yields a mixtute of (3R)-pyrrolidineacetic esters 8 and 9 which are reduced to the corresponding alcohols 10 and 11.Conversion of the alcohols into the sulfonate esters 12 and 13 followed by deprotection of the pyrrolidine nitrogen leads to cyclisation yielding the (4R)-1-azabicycloheptane derivatives 14 and 15.

Production method of (R)-(-)-N-Boc-3-pyrrolidinol

The invention provides a production method of (R)-(-)-N-Boc-3-pyrrolidinol. According to the production method provided by the invention, different solvent media and extraction agents are adopted, theextraction efficiency and the crude product purity are greatly improved, and by the industrial production method, the (R)-(-)-N-Boc-3-pyrrolidinol with the product purity of 98% or above and the total product yield of 70% or above is obtained. Meanwhile, raw materials adopted in the method are easy to obtain, synthesis conditions are simple, the product yield is high, and the method is suitable for industrial production.

NOVEL OXADIAZOLES

The present invention relates to novel compound of Formula I, wherein, R1, A1, A2, A3, A4, A5, L1, A, L2 and R2 are as defined in the detailed description. The present invention also relates to a combination or a composition comprising the compound of Formula I.

A fang chanfu law compound and its preparation method, pharmaceutical composition and use thereof

The invention relates to a new compound for conversion of auricular fibrillation, as shown in the general formula i in the specification (n in the formula is equal to 0 to 4), or pharmaceutically acceptable salt thereof. The invention also provides a novel compound used as a preventive medicine or therapeutic drug for atrial fibrillation, a preparation method and a pharmaceutical composition containing the compound.

Enantioselective α-Benzylation of Acyclic Esters Using π-Extended Electrophiles

The first asymmetric cooperative Lewis base/palladium catalyzed benzylic alkylation of acyclic esters is reported. This reaction proceeds via stereodefined C1-ammonium enolate nucleophiles. Critical to its success was the identification of benzylic phosphate electrophiles, which were uniquely reactive. Alkylated products were obtained with very high levels of enantioselectivity, and this method has been applied toward the synthesis of the thrombin inhibitor DX-9065a.

Methodology Development in Directed Evolution: Exploring Options when Applying Triple-Code Saturation Mutagenesis

Directed evolution of stereo- or regioselective enzymes as catalysts in asymmetric transformations is of particular interest in organic synthesis. Upon evolving these biocatalysts, screening is the bottleneck. To beat the numbers problem most effectively, methods and strategies for building “small but smart” mutant libraries have been developed. Herein, we compared two different strategies regarding the application of triple-code saturation mutagenesis (TCSM) at multiresidue sites of the Thermoanaerobacter brockii alcohol dehydrogenase by using distinct reduced amino-acid alphabets. By using the synthetically difficult-to-reduce prochiral ketone tetrahydrofuran-3-one as a substrate, highly R- and S-selective variants were obtained (92–99 % ee) with minimal screening. The origin of stereoselectivity was provided by molecular dynamics analyses, which is discussed in terms of the Bürgi–Dunitz trajectory.

NOVEL BETULINIC SUBSTITUTED AMIDE DERIVATIVES AS HIV INHIBITORS

The present invention relates to novel betulinic substituted amide compounds of formula (I); and pharmaceutically acceptable salts thereof, wherein R1, R2, R3, R4, R5, R6, R7, R8, X, Y, Z1, Z2, Z3 and are Formula (II) as defined herein. The invention novel betulinic substituted amide derivatives, related compounds, and pharmaceutical compositions useful for the therapeutic treatment of viral diseases and particularly HIV mediated diseases.

AMINOPYRIMIDINE HETEROCYCLIC COMPOUND WITH ADENOSINE RECEPTOR ANTAGONISTIC ACTIVITY

Disclosed hereinis an aminopyrimidine heterocyclic compound with adenosine receptor antagonistic activity, comprising a compound of the general formula (I), or a pharmaceutically acceptable salt thereof. The aminopyrimidine heterocyclic compound with adenosine receptor antagonistic activitydisclosed herein can be used as an effective adenosine receptor antagonist, and can be used for the treatment or prevention of disorders caused by abnormal level of adenosine.

Selection of microbial biocatalysts for the reduction of cyclic and heterocyclic ketones

The reduction of carbonyl compounds plays an important role in the synthesis of complex chiral molecules. In particular, enantiopure substituted cyclic and heterocyclic compounds are useful intermediates for the synthesis of several antiviral, antitumor, and antibiotic agents, and recently, they have also been used as organocatalysts for C-C addition. Alcohol dehydrogenases (ADH) are enzymes involved in the transformation of prochiral ketones to chiral hydroxyl compounds. While significant scientific effort has been paid to the use of aliphatic and exocyclic ketones as ADH substrates, reports on (hetero)cyclic carbonyl compounds as substrates of these enzymes are scarce. In the present study, 109 bacteria and 36 fungi were screened, resulting in 10 organisms belonging to both kingdoms capable of transforming cyclic and heterocyclic ketones into the corresponding alcohols. Among them, Erwinia chrysanthemi could quantitatively reduce cyclododecanone and Geotrichum candidum could stereoselectively reduce N-Boc-3-piperidone and N-Boc-3-pyrrolidinone to their corresponding (S)-alcohols; however, the anti-Prelog isomer was obtained when acetophenone was the substrate.

Stereo-complementary bioreduction of saturated N-heterocyclic ketones

The asymmetric bioreduction of several saturated N-heterocyclic ketones is demonstrated in a stereo-complementary fashion using the ketoreductases READH and ChKRED20 for the production of (S)- and (R)-alcohols, respectively. The reaction accepts substrates with a five-, six- or seven-membered ring, and exhibits excellent stereoselectivity when using 2-propanol as both the ultimate reducing agent and cosolvent, achieve >99% ee in the majority of cases for both enantiomers.