83220-73-9

Usage

Uses

Used in Pharmaceutical Industry:
1-Boc-(R)-(-)-3-Hydroxypyrrolidine is utilized as a chiral building block for the synthesis of various drugs and drug candidates. Its chiral nature and the 1-boc protecting group allow for the development of enantiomerically pure pharmaceuticals, which is essential for ensuring the desired biological activity and minimizing potential side effects.
Used as a Chiral Ligand in Asymmetric Synthesis:
In the field of asymmetric synthesis, 1-Boc-(R)-(-)-3-Hydroxypyrrolidine is employed as a chiral ligand. This application is crucial for the production of enantiomerically pure compounds, which are often necessary for biological activity and to avoid the negative effects associated with the presence of both enantiomers.
Used in the Preparation of Complex Organic Molecules:
1-Boc-(R)-(-)-3-Hydroxypyrrolidine also serves as a building block in the preparation of complex organic molecules. Its unique structure and functional groups make it a valuable component in the synthesis of intricate organic compounds with potential applications in various fields, including materials science, agrochemicals, and fragrances.
Overall, 1-Boc-(R)-(-)-3-Hydroxypyrrolidine is an indispensable chemical reagent in the synthesis of chiral compounds, playing a significant role in advancing the development of pharmaceuticals, fine chemicals, and other specialty products with potential biological activity.

InChI:InChI=1S/C9H17NO3/c1-9(2,3)13-8(12)10-5-4-7(11)6-10/h7,11H,4-6H2,1-3H3/t7-/m1/s1

Upstream product

• 40499-83-0 pyrrolidin-3-ol 
• 58632-95-4 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile 
• 24424-99-5 di-tert-butyl dicarbonate 
• 111810-68-5 3-hydroxypyrrolidine hydrochloride 
• 331442-12-7 (trans)-1-[(1,1-dimethylethoxy)carbonyl]-4-hydroxy-L-proline 
• 40499-83-0 (3R)-pyrrolidinol 
• 101385-93-7 3-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 73286-70-1 N-(tert-butoxycarbonyl)-3-pyrroline 
• 1070-19-5 N-(tert-butyloxycarbonyl) azide 
• 101408-94-0 3R-acetoxypyrrolidine-1-carboxylic acid tert-butyl ester 
• 104706-47-0 (R)-3-hydroxypyrrolidine hydrochloride 
• 123-91-1 1,4-dioxane 
• 100243-39-8 3-hydroxypyrrolidine 
• 132945-74-5 (S)-N-tert-butoxycarbonylpyrrolidin-3-yl benzoate 

Downstream Products

• 518063-52-0 tert-butyl 3-fluoropyrrolidine-1-carboxylate 
• 1572937-18-8 C₁₆H₂₄N₂O₃ 
• 1595291-38-5 tert-butyl 3-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)pyrrolidine-1-carboxylate 
• 1595291-39-6 tert-butyl 5-(tert-butoxycarbonyl(2-(3-(1-(tert-butoxycarbonyl)pyrrolidin-3-yloxy)phenyl)pyrimidin-4-yl)amino)-1H-indazole-1-carboxylate 
• 1595289-86-3 N-(2-(3-(pyrrolidin-3-yloxy)phenyl)pyrimidin-4-yl)-1H-indazol-5-amine 
• 1595291-37-4 tert-butyl 3-(3-bromophenoxy)pyrrolidine-1-carboxylate 
• 1648864-26-9 tert-butyl-3-(2-(tosyloxy)ethoxy)pyrrolidine-1-carboxylate 
• 124817-91-0 tert-butyl (S)-3-(4-cyanophenoxy)pyrrolidine-1-carboxylate 
• 147081-59-2 tert-butyl (3S)-3-(methylamino)pyrrolidine-1-carboxylate 
• 125552-56-9 (S)-tert-butyl 3-azidopyrrolidine-1-carboxylate 
• 1212413-55-2 tert-butyl (R)-3-(2-methoxyethoxy)pyrrolidine-1-carboxylate 
• 109431-87-0 (R)-tert-butyl 3-hydroxypyrrolidine-1-carboxylate 
• 1412975-41-7 (1aR,7bS)-5-[2-((S)-1-ethylpyrrolidin-3-yloxymethyl)-4-fluorobenzene-sulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid 
• 1412979-22-6 methyl (1aR,7bS)-5-[2-((S)-1-ethylpyrrolidin-3-yloxymethyl)-4-fluorobenzene-sulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate 

Relevant academic research and scientific papers

Sustainable Route Toward N-Boc Amines: AuCl3/CuI-Catalyzed N-tert-butyloxycarbonylation of Amines at Room Temperature

N-tert-butoxycarbonyl (N-Boc) amines are useful intermediates in synthetic/medicinal chemistry. Traditionally, they are prepared via an indirect phosgene route with poor atom economy. Herein, a step- and atom-economic synthesis of N-Boc amines from amines, t-butanol, and CO was reported at room temperature. Notably, this N-tert-butyloxycarbonylation procedure utilized ready-made substrates, commercially available AuCl3/CuI as catalysts, and O2 from air as the sole oxidant. This catalytic system provided unique selectivity for N-Boc amines in good yields. More significantly, gram-scale preparation of medicinally important N-Boc amine intermediates was successfully implement, which demonstrated a potential application prospect in industrial syntheses. Furthermore, this approach also showed good compatibility with tertiary and other useful alcohols. Investigations of the mechanisms revealed that gold catalyzed the reaction and copper acted as electron transfer mediator in the catalytic cycle.

Enantioselective reduction of heterocyclic ketones with low level of asymmetry using carrots

A whole spectrum of biocatalysts for asymmetric reduction of prochiral ketones is well known including the Daucus carota root. However, this type of reaction is still challenging when pro-chiral ketones present low level of asymmetry, like heterocyclic ketones. In this work, 4,5-dihydro-3(2H)-thiophenone (1), 2-methyltetrahydrofuran-3-one (2), N-Boc-3-pyrrolidinone (3), 1-Z-3-pyrrolidinone (4) and 1-benzyl-3-pyrrolidinone (5) were studied in order to obtain the respective enantioselective heterocyclic secondary alcohols. Except for 5, the corresponding alcohols were obtained in high values of conversion and with high selectivity. In order to circumvent the low isolated yield of the corresponding chiral alcohol from 2, we observed that the use of carrots in the absence of water is feasible. Addition of co-solvents was needed to the water-insoluble ketones 3 and 4. Comparatively, baker’s yeast was used for bio reductions of 1, 3 and 4. And in terms of conversion, selectivity and work-up, the use of carrots were a more efficient biocatalyst, as well as a viable method for obtaining 5-member heterocyclic secondary alcohols.

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.

Erbium-Catalyzed Regioselective Isomerization-Cobalt-Catalyzed Transfer Hydrogenation Sequence for the Synthesis of Anti-Markovnikov Alcohols from Epoxides under Mild Conditions

Herein, we report an efficient isomerization-transfer hydrogenation reaction sequence based on a cobalt pincer catalyst (1 mol %), which allows the synthesis of a series of anti-Markovnikov alcohols from terminal and internal epoxides under mild reaction conditions (≤55 °C, 8 h) at low catalyst loading. The reaction proceeds by Lewis acid (3 mol % Er(OTf)3)-catalyzed epoxide isomerization and subsequent cobalt-catalyzed transfer hydrogenation using ammonia borane as the hydrogen source. The general applicability of this methodology is highlighted by the synthesis of 43 alcohols from epoxides. A variety of terminal (23 examples) and 1,2-disubstituted internal epoxides (14 examples) bearing different functional groups are converted to the desired anti-Markovnikov alcohols in excellent selectivity and yields of up to 98%. For selected examples, it is shown that the reaction can be performed on a preparative scale up to 50 mmol. Notably, the isomerization step proceeds via the most stable carbocation. Thus, the regiochemistry is controlled by stereoelectronic effects. As a result, in some cases, rearrangement of the carbon framework is observed when tri-and tetra-substituted epoxides (6 examples) are converted. A variety of functional groups are tolerated under the reaction conditions even though aldehydes and ketones are also reduced to the respective alcohols under the reaction conditions. Mechanistic studies and control experiments were used to investigate the role of the Lewis acid in the reaction. Besides acting as the catalyst for the epoxide isomerization, the Lewis acid was found to facilitate the dehydrogenation of the hydrogen donor, which enhances the rate of the transfer hydrogenation step. These experiments additionally indicate the direct transfer of hydrogen from the amine borane in the reduction step.

Diverse functionalization of strong alkyl C–H bonds by undirected borylation

The selective functionalization of strong, typically inert carbon-hydrogen (C–H) bonds in organic molecules is changing synthetic chemistry. However, the undirected functionalization of primary C–H bonds without competing functionalization of secondary C–H bonds is rare. The borylation of alkyl C–H bonds has occurred previously with this selectivity, but slow rates required the substrate to be the solvent or in large excess. We report an iridium catalyst ligated by 2-methylphenanthroline with activity that enables, with the substrate as limiting reagent, undirected borylation of primary C–H bonds and, when primary C–H bonds are absent or blocked, borylation of strong secondary C–H bonds. Reactions at the resulting carbon-boron bond show how these borylations can lead to the installation of a wide range of carbon-carbon and carbon-heteroatom bonds at previously inaccessible positions of organic molecules.

NOVEL COMPOUNDS FOR INHIBITION OF JANUS KINASE 1

An object of the invention is to provide compounds as selective JAK1 inhibitor, a process for preparation of the inhibitors, a composition containing the compounds and utility of the compounds.

PDE9 inhibitor and application thereof

The invention belongs to the technical field of medicine and particularly relates to a PDE9 inhibitor compound shown as formula (I) or its pharmaceutically acceptable salts and stereoisomers, as wellas pharmaceutical preparations and pharmaceutical compositions of these compounds, and their application. The compounds herein are applicable to the preparation of drugs to treat or prevent PDE9-mediated related diseases.

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.