71461-30-8

Usage

Uses

Used in Pharmaceutical Synthesis:
2α-Formylpyrrolidine-1-carboxylic acid benzyl ester is used as a key intermediate in the synthesis of various pharmaceuticals and organic compounds. Its unique structure and versatile reactivity allow for the creation of a wide range of biologically active molecules, contributing to the development of new drugs and therapeutic agents.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, 2α-Formylpyrrolidine-1-carboxylic acid benzyl ester is used as a starting material for the exploration of new antiviral and antibacterial agents. Its potential in this area makes it an important compound for further research and development, with the aim of discovering novel treatments for viral and bacterial infections.
Used in Drug Design and Development:
2α-Formylpyrrolidine-1-carboxylic acid benzyl ester is utilized as a building block in drug design and development, thanks to its functional group compatibility and ability to form various drug-like molecules. Its incorporation into drug candidates can enhance their pharmacological properties, such as potency, selectivity, and bioavailability, ultimately leading to more effective therapeutic agents.
Used in Chemical Synthesis Industry:
In the chemical synthesis industry, 2α-Formylpyrrolidine-1-carboxylic acid benzyl ester is employed as a versatile reactant for the production of a variety of organic compounds. Its unique structure and reactivity make it suitable for use in various synthetic routes, enabling the synthesis of complex molecules with potential applications in various fields, including pharmaceuticals, agrochemicals, and materials science.

Upstream product

• 6216-63-3 N-Cbz-Prolinol 
• 1148-11-4 N-Benzyloxycarbonyl-L-proline 
• 51207-69-3 1,2-pyrrolidinedicarboxylic acid 2-ethyl 1-(phenylmethyl) ester 
• 72597-18-3 (2R)-(+)-phenylmethyl 2-(hydroxymethyl)pyrrolidine-1-carboxylate 
• 501-53-1 benzyl chloroformate 
• 200499-57-6 (2R,4'S)-N-Benzyloxycarbonyl-2-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)pyrrolidine 
• 200499-52-1 (R)-4-Azido-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-butyric acid methyl ester 
• 200499-54-3 (R)-4-Azido-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-butyraldehyde 
• 200499-55-4 (R)-2-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]pyrrolidine 
• 136963-32-1 methyl 2,3-dideoxy-5,6-O-isopropylidene-4-O-p-tolylsulfonyl-D-erythro-hexonate 
• 68832-13-3 D-prolinol 
• 200499-58-7 (R)-1-benzyloxycarbonyl-2-[(S)-1,2-dihydroxyethyl]pyrrolidine 
• 182210-00-0 methyl (2R)-(benzyloxycarbonyl)pyrrolidine-2-carboxylate 
• 61350-60-5 (S)-benzyloxycarbonyl-proline acid chloride 

Downstream Products

• 154659-23-1 (2S)-1-(benzyloxycarbonyl)-2-<(1R,2R)-1,2-dihydroxy-4-phenylbutyl>pyrrolidine 
• 108142-90-1 tert-butyl (βS, 2S)-1-(benzyloxycarbonyl)-2-pyrrolidinehydracrylate 
• 141045-64-9 (2S,1'S,2'S)-N-(Benzyloxycarbonyl)-2-<1'-hydroxy-2'-(phenylthio)-3'-butenyl>pyrrolidine 
• 141116-76-9 (2S,1'R,2'R)-N-(Benzyloxycarbonyl)-2-<1'-hydroxy-2'-(phenylthio)-3'-butenyl>pyrrolidine 
• 138802-18-3 (S)-2-[(1R,2R)-1-Hydroxy-2-methyl-3-((4R,5S)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-yl)-3-oxo-propyl]-pyrrolidine-1-carboxylic acid benzyl ester 
• 108807-54-1 Z-L-prolinal semicarbazone 
• 6216-63-3 N-Cbz-Prolinol 
• 105089-87-0 benzyl (2S)-2-[di(ethylsulfanyl)methyl]tetrahydro-1H-1-pyrrolecarboxylate 
• 128414-09-5 (2S)-1-(benzyloxycarbonyl)-2-<1,2-dihydroxy-4-methylpentyl>pyrrolidine 
• 128414-09-5 (2S)-1-(benzyloxycarbonyl)-2-<(1R,2R)-1,2-dihydroxy-4-methylpentyl>pyrrolidine 
• 110562-20-4 Cbz-Pro-L-prolinal dimethyl acetal 
• 820994-17-0 (Z)-3-[(2'S)-N-benzyloxycarbonylpyrrolidin-2'-yl]propenoate 
• 143771-07-7 benzyl (S)-2-(2-oxoethyl)pyrrolidine-1-carboxylate 
• 1148-11-4 N-Benzyloxycarbonyl-L-proline 

Relevant academic research and scientific papers

Synthesis of chiral branched allylamines through dual photoredox/nickel catalysis

Allylamines are versatile building blocks in the synthesis of various naturally occurring products and pharmaceuticals. In contrast to terminal allylamines, the methods of synthesis of their branched congeners with internal, stereodefined double bonds are less explored. This work describes a new approach for the preparation of allylaminesviacross-coupling of alkyl bromides with simple 3-bromoallylamines by merging the photoredox approach and Ni catalysis. The reaction proceeds under mild conditions, under blue light irradiation, and in the presence of an organic dye, 4CzIPN, as a photocatalyst. The scope of suitable reaction partners is broad, including alkyl bromides bearing reactive functionalities (e.g., esters, nitriles, aldehydes, ketones, epoxides) andN-protected allylamines, as well asN-allylated secondary and tertiary amines and heterocycles. The employment of non-racemic starting materials allows for rapid and easy construction of complex multifunctional allylamine derivatives without the loss of enantiomeric purity.

A novel method to produce synthetic murine CXCL10 for efficient screening of functional variants

Antitumor immune responses depend on the infiltration of solid tumors by effector T cells, a process guided by chemokines. In particular, the chemokine CXCL10 has been shown to play a critical role in mediating recruitment of CXCR3 + cytolytic T and NK ce

Efficient synthesis of methyl (S)-4-(1-methylpyrrolidin-2-YL)-3-oxobutanoate as the key intermediate for tropane alkaloid biosynthesis with optically acitve form

Methyl (S)-4-(1-methylpyrrolidin-2-yl)-3-oxobutanoate has been synthesized for enzymatic studies on cyclization enzymes during cocaine biosynthesis in Erythroxylum coca plants. During the present new synthesis, L-proline was first protected with Cbz group and reduced to chiral amino alcohol, which were then followed by Swern oxidation, Wittig reaction and decarboxylative condensation. At the last step, N-methylamino acid precursor was treated with 1,1'-carbonyldiimidazole followed by reacting with methyl potassium malonate to give the 3-oxobutanoate in 54% overall yield. This new strategy has proven to avoid obvious racemization of the L-proline chiral center during the synthesis. In addition, six of the eight synthesis steps were performed via GAP chemistry/technology without the use of column chromatography for purification.

Selective Aerobic Oxidation of Primary Alcohols to Aldehydes

The 2-azaadamantane- N -oxyl (AZADO)- and 9-azanoradamantane- N -oxyl (nor-AZADO)-catalyzed selective oxidation of primary alcohols to the corresponding aldehydes is described. The use of tert -butyl nitrite as the co-catalyst enables efficient aerobic oxidation in MeCN instead of previously reported AcOH; this is important for the selectivity of the reaction. The addition of a solution of saturated aqueous NaHCO 3 after the completion of the reaction was effective to suppress the overoxidation of the product to the corresponding carboxylic acid during the workup.

FUMAGILLOL HETEROCYCLIC COMPOUNDS AND METHODS OF MAKING AND USING SAME

Disclosed herein, in part, are fumagillol compounds and methods of use in treating medical disorders, such as obesity. Pharmaceutical compositions and methods of making fumagillol compounds are provided. The compounds are contemplated to have activity against methionyl aminopeptidase 2.

Mechanistic insight into aerobic alcohol oxidation using NOx-nitroxide catalysis based on catalyst structure-activity relationships

The mechanism of an NOx-assisted, nitroxide(nitroxyl radical)-catalyzed aerobic oxidation of alcohols was investigated using a set of sterically and electronically modified nitroxides (i.e., TEMPO, AZADO (1), 5-F-AZADO (2), 5,7-DiF-AZADO (3), 5-MeO-AZADO (4), 5,7-DiMeO-AZADO (5), oxa-AZADO (6), TsN-AZADO (7), and DiAZADO (8)). The motivation for the present study stemmed from our previous observation that the introduction of an F atom at a remote position from the nitroxyl radical moiety on the azaadamantane nucleus effectively enhanced the catalytic activity under typical NOx-mediated aerobic-oxidation conditions. The kinetic profiles of the azaadamantane-N-oxyl-[AZADO (1)-, 5-F-AZADO (2)-, and 5,7-DiF-AZADO (3)]-catalyzed aerobic oxidations were closely investigated, revealing that AZADO (1) showed a high initial reaction rate compared to 5-F-AZADO (2) and 5,7-DiF-AZADO (3); however, AZADO-catalyzed oxidation exhibited a marked slowdown, resulting in ～90% conversion, whereas 5-F-AZADO-catalyzed oxidation smoothly reached completion without a marked slowdown. The reasons for the marked slowdown and the role of the fluoro group are discussed. Oxa-AZADO (6), TsN-AZADO (7), and DiAZADO (8) were designed and synthesized to confirm their comparable catalytic efficiency to that of 5-F-AZADO (2), providing supporting evidence for the electronic effect on the catalytic efficiency of the heteroatoms under NOx-assisted aerobic-oxidation conditions.

Henry-Nef reaction: A practical and versatile chiral pool route to 2-substituted pyrrolidine and piperidine alkaloids

The paper describes the synergistic protocol developed by combinatorial Henry and Nef reaction for the synthesis of 2-substituted pyrrolidine and piperidine alkaloids containing 1,3-aminoketone and 1,3-amino alcohol units. The utility of the protocol is demonstrated by asymmetric synthesis of 12 natural products of which asymmetric synthesis of (-)-N-methylpelletierine is presented for the first time. The one-carbon homologation described also provides an alternate route for the synthesis of key intermediates homoprolinol and homopipecolinol used as synthetic precursors for several alkaloids and construction of β-amino acids from α-amino acids.

Synthesis of (R)-norbgugaine and its potential as quorum sensing inhibitor against Pseudomonas aeruginosa

(R)-Bgugaine is a natural pyrrolidine alkaloid from Arisarum vulgare, which shows antifungal and antibacterial activity. In this Letter, we have accomplished the simple synthesis of norbgugaine (demethylated form of natural bgugaine) employing Wittig olefination and cat. hydrogenation as the key steps and its biological studies are reported for the first time. The synthesized norbgugaine was evaluated for inhibition of quorum sensing mediated virulence factors (motility, biofilm formation, pyocyanin pigmentation, rhamnolipid production and LasA protease) in Pseudomonas aeruginosa wherein swarming motility is reduced by 95%, and biofilm formation by 83%.

Hybrids of privileged structures benzothiazoles and pyrrolo[2,1-c] [1,4]benzodiazepin-5-one, and diversity-oriented synthesis of benzothiazoles

Privileged structures like Benzothiazole and Pyrrolobenzodiazepine offer wonderful opportunity to explore in anti-cancer drug discovery as a mean to counter drug-resistance problem. BT-PBD hybrids and diverse BT derivatives have been synthesized and their in vitro cytotoxic activities were screened against five cancer cell lines have been discussed. The novel compounds showed promising results as compared with the marketed drug etoposide and could well be used in future anti-cancer drug development studies.

Total synthesis of 1-deoxy-7,8a-di-epi-castanospermine and formal synthesis of pumiliotoxin-251D

A concise and efficient synthesis of (6R,7S,8R,8aS)-6,7,8- trihydroxyindolizidine (1-deoxy-7,8a-di-epi-castanospermine) 2 is described. The synthesis employs cross metathesis in building the key intermediate 9 and is used effectively in constructing indol