854917-80-9

Upstream product

• 142351-11-9 methyl 1-(4-methoxybenzoyl)pyrrolidine-2-carboxylate 
• 824-94-2 p-methoxybenzyl chloride 
• 23356-96-9 (S)-1-Pyrrolidin-2-yl-methanol 
• 147-85-3 L-proline 
• 2577-48-2 methyl (2S)-pyrrolidine carboxylate 
• 100-09-4 4-methoxybenzoic acid 
• 87341-38-6 methyl (2S)-1-(4-methoxybenzyl)pyroglutamate 
• 212393-24-3 (S)-methyl 1-(4-methoxybenzyl)pyrrolidine-2-carboxylate 

Downstream Products

• 23356-96-9 (S)-1-Pyrrolidin-2-yl-methanol 
• 69610-40-8 N-(tert-butoxycarbonyl)-L-prolinol 

Relevant academic research and scientific papers

Transition-Metal-Free Deconstructive Lactamization of Piperidines

One of the major challenges in organic synthesis is the activation or deconstructive functionalization of unreactive C(sp3)–C(sp3) bonds, which requires using transition or precious metal catalysts. We present here an alternative: the deconstructive lactamization of piperidines without using transition metal catalysts. To this end, we use 3-alkoxyamino-2-piperidones, which were prepared from piperidines through a dual C(sp3)–H oxidation, as transitory intermediates. Experimental and theoretical studies confirm that this unprecedented lactamization occurs in a tandem manner involving an oxidative deamination of 3-alkoxyamino-2-piperidones to 3-keto-2-piperidones, followed by a regioselective Baeyer–Villiger oxidation to give N-carboxyanhydride intermediates, which finally undergo a spontaneous and concerted decarboxylative intramolecular translactamization.

Amide activation by Tf2O: Reduction of amides to amines by NaBH4 under mild conditions

An expeditious and practical method for the reduction of amides to amines is reported. The method is consisted of activation of amides with Tf 2O followed by reduction with sodium borohydride in THF at room temperature. Various amides/lactams gave the corresponding amines in good to excellent yields, even with hindered amides and secondary amides. This method also presents other advantages such as TBDPS-group tolerance, short reaction time, simple workup and purification procedure. Georg Thieme Verlag Stuttgart.

Exploiting π shielding interactions of η6 arene chromium (0) complexes: New auxiliaries derived from the biogenic chiral pool

A family of highly selective chiral auxiliaries containing arene chromium (0) complexes has been prepared using biogenic precursors from the chiral pool. The systems, derived from isomannide, prolinol, and xylofuranose were applied to the asymmetric Diels-Alder reaction of derived acrylate esters. Factors influencing stereoselectivity with the auxiliaries have been investigated and delineated including the impact of mixed ligands on the chromium (0) complex. Under optimal conditions, the auxiliaries give >95% e.e. and 98:2 exo:endo ratio in cycloaddition with cyclopentadiene.

Exploiting π-shielding interactions: A highly selective chiral auxiliary derived from a biogenic building block

A chiral auxiliary template, designed on the basis of π-shielding capability has been prepared from readily available L-proline. Cycloaddition to an acrylate derivative gave high endo preference, and diastereoselectivity as high as 99% was attainable. The electronic factors contributing to selectivity were probed, and the technology successfully applied to a polymer supported variant.

Design, synthesis, and biological evaluation of novel T-Type calcium channel antagonists

This paper describes the synthesis of several novel T-type calcium channel antagonists that inhibit calcium influx into the cell, which in turn regulates unknown aspects of the cell cycle pathway that are responsible for cellular proliferation. A library of compounds was synthesized anda brief structure activity relationship will be described. From these studies we have identified a compound (1) that displays anti-proliferative activity in the low micromolar range across a variety of cancer cell lines.