64030-42-8

Upstream product

• 1148-11-4 N-Benzyloxycarbonyl-L-proline 
• 501-53-1 benzyl chloroformate 
• 147-85-3 L-proline 
• 62-53-3 aniline 

Downstream Products

• 1621189-18-1 (S)-2-phenyl-5,6,7,7a-tetrahydro-1H-pyrrolo[1,2-c]imidazol-2-ium hexafluorophosphate 
• 1621189-22-7 (7aS,7'aS,E)-2,2'-diphenyl-1,1',2,2',5,5',6,6',7,7',7a,7'a-dodecahydro-3,3'-bipyrrolo[1,2-c]imidazolylidene 
• 1621189-19-2 C₁₃H₁₆N₂O₂ 
• 1374321-36-4 (S)-1-(2,2,2-trichloroacetyl)-2-(phenylcarbamoyl)pyrrolidine 
• 17360-31-5 (S)-1-benzoyl-2-(phenylcarbamoyl)pyrrolidine 
• 1308264-17-6 (S)-1-pivaloyl-2-(phenylcarbamoyl)pyrrolidine 
• 81968-50-5 2-methyl-1-(2-phenyl-hexahydro-pyrrolo[1,2-c]imidazol-3-yl)-propan-1-one 
• 81968-49-2 1-(2-phenyl-hexahydro-pyrrolo[1,2-c]imidazol-3-yl)-propan-1-one 
• 81968-47-0 phenyl-(2-phenyl-hexahydro-pyrrolo[1,2-c]imidazol-3-yl)-methanone 
• 81968-51-6 5-methyl-1-((7aS)-2-phenyl-(7ar)-hexahydro-pyrrolo[1,2-c]imidazol-3ξ-yl)-hex-5-en-1-one 
• 81968-57-2 3-(2-Bromo-phenyl)-2-phenyl-hexahydro-pyrrolo[1,2-c]imidazole 
• 81968-52-7 1-((S)-2-Phenyl-hexahydro-pyrrolo[1,2-c]imidazol-3-yl)-hex-5-en-1-one 
• 71464-77-2 (E)-3-((S)-2-Phenyl-hexahydro-pyrrolo[1,2-c]imidazol-3-yl)-acrylic acid methyl ester 
• 71350-58-8 methoxycarbonyl aminal 

Relevant academic research and scientific papers

Rational design of simple organocatalysts for the hsicl3 enantioselective reduction of (E)-n-(1-phenylethylidene)aniline

Prolinamides are well-known organocatalysts for the HSiCl3 reduction of imines; however, custom design of catalysts is based on trial-and-error experiments. In this work, we have used a combination of computational calculations and experimental work, including kinetic analyses, to properly understand this process and to design optimized catalysts for the benchmark (E)-N-(1-phenylethylidene)aniline. The best results have been obtained with the amide derived from 4-meth-oxyaniline and the N-pivaloyl protected proline, for which the catalyzed process is almost 600 times faster than the uncatalyzed one. Mechanistic studies reveal that the formation of the component supramolecular complex catalyst-HSiCl3-substrate, involving hydrogen bonding breaking and costly conformational changes in the prolinamide, is an important step in the overall process.

Proline-based carbamates as cholinesterase inhibitors

Series of twenty-five benzyl (2S)-2-(arylcarbamoyl)pyrrolidine-1-carboxylates was prepared and completely characterized. All the compounds were tested for their in vitro ability to inhibit acetylcholinesterase (AChE) and butyrylcholinesterase (BChE), and the selectivity of compounds to individual cholinesterases was determined. Screening of the cytotoxicity of all the compounds was performed using a human monocytic leukaemia THP-1 cell line, and the compounds demonstrated insignificant toxicity. All the compounds showed rather moderate inhibitory effect against AChE; benzyl (2S)-2-[(2-chlorophenyl)carbamoyl]pyrrolidine-1-carboxylate (IC50 = 46.35 μM) was the most potent agent. On the other hand, benzyl (2S)-2-[(4-bromophenyl)-] and benzyl (2S)-2-[(2-bromophenyl)carbamoyl]pyrrolidine-1-carboxylates expressed anti-BChE activity (IC50 = 28.21 and 27.38 uM, respectively) comparable with that of rivastigmine. The ortho-brominated compound as well as benzyl (2S)-2-[(2-hydroxyphenyl)carbamoyl]pyrrolidine-1-carboxylate demonstrated greater selectivity to BChE. The in silico characterization of the structure-inhibitory potency for the set of proline-based carbamates considering electronic, steric and lipophilic properties was provided using comparative molecular surface analysis (CoMSA) and principal component analysis (PCA). Moreover, the systematic space inspection with splitting data into the training/test subset was performed to monitor the statistical estimators performance in the effort to map the probability-guided pharmacophore pattern. The comprehensive screening of the AChE/BChE profile revealed potentially relevant structural and physicochemical features that might be essential for mapping of the carbamates inhibition efficiency indicating qualitative variations exerted on the reaction site by the substituent in the 3′-/4′-position of the phenyl ring. In addition, the investigation was completed by a molecular docking study of recombinant human AChE.

An optimized and scalable synthesis of propylphosphonic anhydride for general use

Abstract Propylphosphonic anhydride (T3P) is an effective coupling and dehydrating agent, which has been used for a large number of chemical transformations. An efficient and versatile synthetic method is described to synthesize propylphosphonic anhydride (T3P) in pure form, in an overall yield of 51% in four steps from commercially available diethyl phosphonate.

Synthesis and characterization of new chiral azolinium salts, precursors to N-heterocyclic carbenes, derived from l-proline

A short and flexible procedure for the preparation of seven chiral azolinium and five functionalized chiral azolinium salts, precursors to N-heterocyclic carbenes, derived from l-proline has been developed. Moderate to good overall yields were obtained. Some NHC dimers and thiones were isolated. X-ray crystal structure determinations of two [Rh-NHC] complexes were also reported.

Amides in one pot from Carboxylic Acids and Amines via Sulfinylamides

An efficient method has been developed for the direct amidification of carboxylic acids via sulfinylamides preformed in situ by the reaction of pure amines with prop-2- ene-1-sulfinyl chloride. The method can be applied to aliphatic acids, including pivalic acid, aromatic acids, and primary and secondary amines. It is compatible with acids bearing unprotected alcohol, phenol, and ketone moieties and applicable to the synthesis of peptides. It does not induce their a-epimerization.

A simple proline-based organocatalyst for the enantioselective reduction of imines using trichlorosilane as a reductant

A simple and inexpensive proline-based organocatalyst was developed for the reduction of imines using trichlorosilane as a reductant. The reduction of N-aryl imines in the presence of 10 mol % of N-pivaloyl-l-proline anilide was carried out to give the co

Evaluation of ligands for ketone reduction by asymmetric hydride transfer in water by multi-substrate screening

Various ligands for the ruthenium-catalyzed enantioselective reduction of ketones in water have been investigated. Multi-substrate reactions have been carried out for the comparison of various proline amides and aminoalcohol ligands. Two sets of six aromatic ketones have been selected in order to evaluate the enantiomeric excesses of all the resulting alcohols by a single chromatographic analysis. The proline amide derivative prepared from (1R,2S)-cis-aminoindanol revealed as the best ligand for most of the ketones used in the multi-substrate reductions. This ligand has been employed for the enantioselective reduction of a variety of other aromatic ketones and in all cases the enantiomeric excesses were improved compared to those obtained with phenylprolineamide used in our previous work.

Method for preparing 2-(2-arylmorpholin-2-yl)ethanol derivatives and intermediates

The invention relates to a process for the preparation of substituted 2-(2-arylmorpholin-2-yl)ethanol derivatives.

Small organic molecule catalyzed enantioselective direct aldol reaction in water

Protonated pyrrolidine based small organic molecules have been designed and evaluated for the asymmetric direct aldol reaction in water. The designed organocatalysts are multifunctional in nature and exploit the combined effect of hydrogen bonding and hydrophobic interactions for enantioselective catalysis in water. As a result a unique direct asymmetric aldol reaction in water catalyzed by a small organic molecule having an amide linkage has been developed. The developed catalyst affords chiral β-hydroxyketones in good yields (93%) and enantioselectivities (upto 62%) in water.

Use of amino amides derived from proline as chiral ligands in the ruthenium(II)-catalyzed transfer hydrogenation reaction of ketones

We developed an efficient, easily available, and easy to use proline amide-based ruthenium(II) catalysts for the asymmetric hydride transfer reduction of prochiral ketones and e.e.s up to 98.8% have been measured.