122151-38-6

Basic information

• Product Name: 1-[(2S-)-2-Hydroxy-1-oxo-proxyl]pyrrolidine
• Synonyms: 1-[(2S-)-2-Hydroxy-1-oxo-proxyl]pyrrolidine;Pyrrolidine, 1-[(2S)-2-hydroxy-1-oxopropyl]- (9CI);(S)-2-hydroxy-1-(pyrrolidin-1-yl)propan-1-one;(S)-N,N-TetraMethylene-lactaMide;1(2S)(2-HYDROXY-1-OXOPROPYL)PYRROLIDINE;(S)-1-(pyrrolidin-1-yl)-2-hydroxypropan-1-one
• CAS NO: 122151-38-6
• Molecular Formula: C₇H₁₃NO₂
• Molecular Weight: 143.18362
• EINECS: 601-833-8
• Product Categories: ACETYLGROUP
• Mol File: 122151-38-6.mol

Chemical Properties

• Boiling Point: 282.498°C at 760 mmHg
• Flash Point: 124.651°C
• Appearance: /
• Density: 1.142g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.507
• Storage Temp.: 2-8°C
• PKA: 13.65±0.20(Predicted)
• CAS DataBase Reference: 1-[(2S-)-2-Hydroxy-1-oxo-proxyl]pyrrolidine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[(2S-)-2-Hydroxy-1-oxo-proxyl]pyrrolidine(122151-38-6)
• EPA Substance Registry System: 1-[(2S-)-2-Hydroxy-1-oxo-proxyl]pyrrolidine(122151-38-6)

Safety Data

• Hazardous Substances Data: 122151-38-6(Hazardous Substances Data)

Usage

Uses

Used in Chemical Research:
1-[(2S-)-2-Hydroxy-1-oxo-proxyl]pyrrolidine is used as a research compound for studying its chemical properties and potential applications in various fields.
Used in Pharmaceutical Industry:
1-[(2S-)-2-Hydroxy-1-oxo-proxyl]pyrrolidine is used as a potential drug candidate for its possible therapeutic applications, given its unique structure and functional groups.
Used in Material Science:
1-[(2S-)-2-Hydroxy-1-oxo-proxyl]pyrrolidine is used as a component in the development of new materials, potentially benefiting from its stable free radical properties and its interaction with other molecules.

InChI:InChI=1/C7H13NO2/c1-6(9)7(10)8-4-2-3-5-8/h6,9H,2-5H2,1H3/t6-/m0/s1

Upstream product

• 123-75-1 pyrrolidine 
• 687-47-8 (S)-Ethyl lactate 
• 79-33-4 L-Lactic acid 
• 1532548-78-9 1-(prop-2-ene-1-sulfinyl)pyrrolidine 
• 27871-49-4 (S)-Methyl lactate 
• 109-97-7 pyrrole 

Downstream Products

• 566202-91-3 (1'R)-[2-(4-benzyloxybenzyloxy)-5-bromophenyl]acetic acid 1'-methyl-2'-oxo-2'-pyrrolidin-1'-ylethyl ester 
• 930779-79-6 (2S)-1-oxo-1-(pyrrolidin-1-yl)propan-2-yl 2-bromo-2-(4-chlorophenyl)acetate 
• 2387-23-7 1,3-Dicyclohexylurea 
• 1187307-97-6 (2S)-1-(pyrrolidin-1-yl)propan-2-ol 
• 122151-32-0 (S)-2-(benzyloxy)-1-(pyrrolidin-1-yl)propan-1-one 
• 1283147-55-6 (R)-1-oxo-1-(pyrrolidin-1-yl)propan-2-yl 2-(2-(benzyloxy)-3-methoxyphenyl)acetate 

Relevant articles and documents

Asymmetric synthesis of arylpropionic acids and aryloxy acids by using lactamides as chiral auxiliaries

Two different dynamic kinetic resolution methods have been applied for the asymmetric synthesis of pharmaceutical arylpropionic acids and aryloxy acids by using amides of (S)-lactic acid as chiral auxiliaries. For arylpropionic acids the esterification mediated by dicyclohexylcarbodiimide (DCC) and 4-(dimethylamino)pyridine (DMAP) proceeds with good asymmetric induction, while for aryloxyacetic acids the keystep is a diastereoselective substitution reaction in the presence of triethylamine and n-hexylammonium iodide as additives. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

Stereoselective synthesis of 2-aryloxy acids from lactamide derived esters of racemic α-halo carboxylic acids

Pyrrolidine derived (S)-lactamide auxiliaries mediate a highly stereoselective coupling reaction between racemic α-haloacids and aryloxides. These amide auxiliaries exhibit enhanced rates of reaction as well as increased degrees of diastereoselection over

A PROCESS FOR THE MANUFACTURE OF POSACONAZOLE

The present invention discloses an improved process for the manufacture of Posaconazole, an anti-fungal agent belonging to the category of substituted Tetrahydrofuran Triazole compound. The present invention further describes preparation of formula A and formula B, the key intermediates in the preparation of Posaconazole. The invention also discloses novel intermediates that are useful in the synthesis of Posaconazole.

Preparation method of posaconazole intermediate

The invention discloses a preparation method of a key intermediate POB for preparing posaconazole. Firstly, BP004b04 and oxalic acid are salified to obtain POE; secondly, the POE reacts with di-tert-butyl dicarbonate in the presence of a base to obtain POP, and the POP is recrystallized; thirdly, the POP and POK react with each other in the presence of a base to obtain POR, and POS is obtained after a tert-butyl carbonate protecting group of the POR is removed; finally, the POS is subjected to ring closure to obtain the POB. By means of the method, in the obtained POB, the content of diastereomers is smaller than or equal to 0.01%, and the total yield of the entire route is high.

Preparation method of high-purity posaconazole

The invention discloses a preparation method of posaconazole, comprising: subjecting BP004b04 and oxalic acid to salt forming to obtain POE; subjecting POE and di-tert-butyl decarbonate to reaction inthe presence of a base to obtain POP, and recrystallizing POP; subjecting POP and POK o reaction in the presence of a base to obtain POR, and removing tert-butyl carbonate protecting group from POR to obtain POS; subjecting the POS to ring closing to obtain POB; subjecting the POB and POA to reaction to obtain posaconazole. Posaconazole prepared via the preparation method has the content of diastereoisomers being /=0.01%, and the overall route has high total yield.

Intermediate for preparing posaconazole

The invention discloses an intermediate POP for preparing posaconazole. A structure of the intermediate is as shown in the specification. By using the intermediate to prepare POB, the obtained POB hasa diastereomer content being smaller than or equal to 0.01%, and the total yield of the overall route is relatively high.

Toward Chromanes by de Novo Construction of the Benzene Ring

The work describes three principal Diels-Alder cycloaddition approaches toward chromanes that are designed for the de novo construction of the benzene ring. This study specifically focuses on the potential exploitation in the total synthesis of chromane-bearing natural products such as cebulactam A.

Efficient Stereoselective Synthesis of a Key Chiral Aldehyde Intermediate in the Synthesis of Picolinamide Fungicides

A highly stereoselective and efficient synthesis of (4S,5S,6S)-6-(benzyloxy)-5-phenoxy-4-propoxyheptanal, a key intermediate for syntheses of picolinamide fungicides, is described in this report. The synthesis features a scalable allylpropyl ether preparation, an efficient synthesis of the C1-C3 anti,syn-(S,S,S) stereotriad via a highly diastereoselective allylboration, and Cu-catalyzed phenylation of a sterically hindered secondary alcohol with BiPh3(OAc)2 followed by highly regioselective hydroformylation with the formation of a linear aldehyde. Excellent overall route efficiency was achieved (six steps and 39% yield) starting from readily available and inexpensive (S)-ethyl lactate.

Total synthesis of (+)-herboxidiene/GEX 1A

A total synthesis of (+)-herboxidiene/GEX 1A has been accomplished from (R)- and (S)-lactate esters in a highly efficient manner. Key steps of the synthesis involve substrate-controlled titanium-mediated aldol reactions from chiral lactate-derived ethyl ketones, an oxa-Michael cyclization, an Ireland-Claisen rearrangement, and a Suzuki coupling. Furthermore, computational studies of the oxa-Michael reaction have unveiled the dramatic influence of intramolecular hydrogen bonds on the stereochemical outcome of such cyclizations, whereas biological analyses have clearly proved the important cytoxicity of (+)-herboxidiene/GEX 1A.

Total Synthesis and Absolute Configuration of Raputindole A

The first total synthesis of the bisindole alkaloid raputindole A from the rutaceous plant Raputia simulans is reported. The key step is a Au(I)-catalyzed cyclization that assembles the cyclopenta[f]indole tricycle from a 6-alkynylated indoline precursor. The isobutenyl side chain was installed by Suzuki-Miyaura cross-coupling, followed by a regioselective reduction employing LiDBB. Starting from 6-iodoindole, the sequence needs nine steps and provided (±)-raputindole A in 6.6% overall yield. The absolute configuration of the natural product (+)-raputindole A was determined by quantum chemical calculation of the ECD spectrum.