62624-45-7

Upstream product

• 252338-34-4 ethyl 2-pyrrolidinone-3-carboxylate 
• 92119-61-4 4-phenyl-1,5-dihydro-2H-pyrrol-2-one 
• 52784-31-3 3-Phenylcyclobutanone 
• 100-42-5 styrene 
• 84872-79-7 4-amino-3-phenylbutanoic acid methyl ester 
• 103-26-4 Methyl cinnamate 
• 34687-03-1 4-nitro-3-phenylbutanoic acid methyl ester 
• 6626-84-2 dimethyl 2-benzylidenepropanedioate 
• 77519-55-2 2-oxo-4-phenylpyrrolidine-3-carboxylic acid 
• 55790-17-5 3-methoxycarbonyl-4-phenyl-2-pyrrolidone 
• 55790-16-4 (2-nitro-1-phenyl-ethyl)-malonic acid dimethyl ester 
• 100-52-7 benzaldehyde 
• 1431854-83-9 C₁₂H₁₇NO₂ 
• 1431854-82-8 C₁₂H₁₅N₃O₂ 

Downstream Products

• 62624-46-8 (S)-(+)-3-phenylpyrrolidine 
• 128372-78-1 (-)-(S)-1-tert-Butoxycarbonyl-4-phenyl-2-pyrrolidinone 

Relevant academic research and scientific papers

Optical resolution of cyclic amides by inclusion in dehydrocholic acid

Dehydrocholic acid serves as an effective chiral host for the resolution of several five-, six-, and seven-membered cyclic amides by inclusion.

Catalytic enantioselective conjugate addition of cyanide to α,β-unsaturated N-acylpyrroles

A catalytic enantioselective conjugate addition of cyanide to α,β-unsaturated N-acylpyrroles was developed using the chiral gadolinium catalyst generated from Gd(OiPr)3 and D-glucose-derived ligand 2. Generally high enantioselectivit

Desymmetrization of Prochiral Cyclobutanones via Nitrogen Insertion: A Concise Route to Chiral γ-Lactams

Asymmetric access to γ-lactams is achieved via a cyclobutanone ring expansion using widely available (1S,2R)-1-amino-2-indanol for chiral induction. Mechanistic analysis of the key N,O-ketal rearrangement reveals a Curtin–Hammett scenario, which enables a downstream stereoinduction (up to 88:12 dr) and is corroborated by spectroscopic, crystallographic, and computational studies. In combination with an easy deprotection protocol, this operationally simple sequence allows the synthesis of a range of optically pure γ-lactams, including those bearing all-carbon quaternary stereocenters. In addition, the formal synthesis of drug molecules baclofen, brivaracetam, and pregabalin further demonstrates the synthetic utility and highlights the general applicability of the presented method.

Substituted 1-methyl-4-phenylpyrrolidin-2-ones – Fragment-based design of N-methylpyrrolidone-derived bromodomain inhibitors

N-Methylpyrrolidone is one of several chemotypes that have been described as a mimetic of acetyl-lysine in the development of bromodomain inhibitors. In this paper, we describe the synthesis of a 4-phenyl substituted analogue – 1-methyl-4-phenylpyrrolidin-2-one – and the use of aryl substitution reactions as a divergent route for derivatives. Ultimately, this has led to structurally complex, chiral compounds with progressively improved affinity as inhibitors of bromodomain-containing protein 4.

Highly Enantioselective Synthesis of Chiral γ-Lactams by Rh-Catalyzed Asymmetric Hydrogenation

A Rh/bisphosphine-thiourea (ZhaoPhos) catalytic system has been identified for the straightforward asymmetric synthesis of chiral γ-lactams. A variety of NH free α,β-unsaturated lactams bearing a β-aryl or β-alkyl substituent were smoothly hydrogenated to

Efficient synthesis of β-aryl-γ-lactams and their resolution with (S)-Naproxen: Preparation of (R)- and (S)-Baclofen

An efficient synthesis of enantiomerically-pure β-aryl-γ-lactams is described. The principal feature of this synthesis is the practical resolution of β-aryl-γ-lactams with (S)-Naproxen. The procedure is based on the Michael addition of nitromethane to benzylidenemalonates, which was easily obtained, followed by the reduction of the γ-nitroester in the presence of Raney nickel and the subsequent saponification/decarboxylation reaction. The utility of this methodology was highlighted by the preparation of enantiomerically-pure (R)- and (S)-Baclofen hydrochloride.

BENZAMIDE CGRP RECEPTOR ANTAGONISTS

The present invention is directed to benzamide compounds which are antagonists of CGRP receptors and useful in the treatment or prevention of diseases in which CGRP is involved, such as migraine. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which CGRP is involved.

Multisite organic-inorganic hybrid catalysts for the direct sustainable synthesis of GABAergic drugs

Multisite organic-inorganic hybrid catalysts have been prepared and applied in a new general, practical, and sustainable synthetic procedure toward industrially relevant GABA derivatives. The domino sequence is composed of seven chemical transformations which are performed in two one-pot reactions. The method produces both enantiomeric forms of the product in high enantiopurity as well as the racemate in good yields after a single column purification step. This protocol highlights major process intensification, catalyst recyclability, and low waste generation.

Studies on the chemoenzymatic synthesis of 3-phenyl-GABA and 4-phenyl-pyrrolid-2-one: The influence of donor of the alkoxy group on enantioselective esterification

A new chemoenzymatic method for the synthesis of enantiomerically pure 3-phenyl-γ-aminobutyric acid 1 and 4-phenyl-pyrrolid-2-one 9 based on the enzymatic kinetic resolution of 3-phenyl-4-pentenoic acid 2 is described herein. Enzymatic resolution of the r

Lewis acid catalyzed highly stereoselective domino-ring-opening cyclization of activated aziridines with enolates: Synthesis of functionalized chiral γ-lactams

Figure presented. A highly enantio- and diastereoselective Lewis acid catalyzed SN2-type ring opening followed by cyclization of aziridines with active methylene carbon nucleophiles to functionalized chiral γ-lactams in a domino fashion has been developed. γ-Lactams have been desulfonated and decarboxylated, providing pyrrolidone-3-carboxylate and N-tosylpyrrolidinone derivatives, respectively, in good yields.