Showing papers in "Organic Process Research & Development in 2004"

TL;DR: A bridging function is needed to bring the vast amount of findings documented to a compact format and to compare it to the state of the art in the chemicals-producing industry.

TL;DR: The micro-reactor technology is an efficient tool for kilogram-scale syntheses in continuous mode and is particularly effective for hazardous reactions that do not allow scale-up in conventional reactors as mentioned in this paper.

TL;DR: In this article, the metastable zone is generated automatically by linking a laser backscattering probe to an automated laboratory reactor, and the evolution of solution concentration and supersaturation is determined by transmitting data from an in situ total reflectance Fourier transform infrared (ATR-FTIR) spectroscope to the laboratory reactor.

TL;DR: A reagent-controlled stereoselective boron enolate aldol reaction between 2 and 3 forming the C7 hydroxyl-bearing stereocenter, selective reduction of 4a to generate the 1,3-anti-diol 5, and a global deprotection and concomitant lactonization leading to (+)-discodermolide are highlighted.

TL;DR: In this paper, a case study of a continuous multistep process is presented, where micro-reaction technology is used to reduce the cost of process development and manufacturing of active pharmaceutical ingredients and other functional molecules on a commercial scale.

TL;DR: A series of synthetic transformations were successfully and safely scaled up to multigram quantities using focused microwave irradiation with a continuous flow reaction cell that was developed in-house and which can be easily adapted to commercially available instrumentation as discussed by the authors.

TL;DR: In this paper, a continuous microflow system was developed with efficient catalyst recycling for a Mizoroki−Heck reaction of iodobenzene with butyl acrylate, using a low-viscosity ionic liquid ([bmim]NTf2) as the...

TL;DR: In this paper, a multikilogram preparation of α-methyl aldehyde 10 from Roche ester, its syn-aldol reaction with Evans boron enolate, removal of the chiral auxiliary, and the preparation of Weinreb amide 3 (Smith common precursor) was presented without any chromatography.

TL;DR: In this paper, a one-pot oxidation from cyclohexane to adipic acid has been developed, catalyzed by Fe−porphyrin in the presence of molecular oxygen without any additives.

TL;DR: A second generation manufacturing process from a shikimic acid-derived epoxide to oseltamivir phosphate features a magnesium chloride−amine complex-catalyzed ring opening of the epoxide by tert-butylamine as mentioned in this paper.

TL;DR: In this paper, an industrial production-scale process currently conducted at Clariant site/Frankfurt, termed Phenyl Boronic acid process from here on, was investigated at laboratory-scale using two micromixer/tubular reactor configurations, being equipped with either a glass interdigital (for details see (1) Ehrfeld, W.; Golbig, K.; Hessel, V.; Lowe, H.; Richter, T.).

TL;DR: The enantioselective conversion of racemic PED by Candida parapsilosis CCTCC M203011 was found to be the most efficient process to produce (S)-PED with high optical purity of 98% ee and yield of 92%.

TL;DR: In this article, the Suzuki-type coupling conditions employed by Marshall (5a/tert-BuLi/B-OMe-9-BBN added to 4/Cs2CO3/Pd(dppf)2) were used to produce the cis-trisubstituted olefin.

TL;DR: In this article, a simpler and more efficient alternative to the Schiff base-mediated formation of sertraline imine has been developed and is presented in this paper, where the condensation reaction between 4-(3,4-dichlorophenyl)-3, 4-dihydro-1(2H)-naphthalone, sERTraline tetralone, and monomethylamine was carried out in ethanol, without the need for classical dehydrating agent such as TiCl4, or more novel approaches, such as molecular sieves,

TL;DR: In this paper, five pharmaceutical materials, including two salts and three neutral compounds, have been subjected to nanoindentation analysis on a single-crystal scale and the results were used to calculate a brittleness index for each of the five materials.

TL;DR: In this article, the production of diphenyl carbonate (DPC) by the transesterification of dimethyl carbonate with phenol was performed using a variety of solid catalysts.

TL;DR: In this article, the authors described a kilogram-scale synthesisation of fragments C1-6 (6) and C9-14 (4) of (+)-discodermolide from common precursor 3.

TL;DR: In this paper, the selectivity of the aerobic oxidation of 4,4'-diisopropyldiphenyl and 2,6'diisophropylnaphthalene was investigated on a quantitative kinetic basis.

TL;DR: In this article, the hydrogenation of three different pharmaceutical nitro-containing compounds has been studied using high-throughput experimentation (HTE) methods, and significant improvements to the existing reactions were obtained for two of the examples.

TL;DR: In this article, four process research investigations are directed toward discerning a scalable, enantioselective method for preparing (S)-β-amino acid ester 3, a key intermediate to the αvβ3 integrin antagonist 1.

TL;DR: In this article, a convenient, optimized and safe synthesis of N-arylhydrazines, useful as intermediates for active ingredients in agricultural and pharmaceutical applications, was reported, starting from aryl halid...

TL;DR: Fiduxosin (1) has been under development at Abbott Laboratories for the treatment of benign prostatic hyperplasia as discussed by the authors, and a convergent strategy required methodologies for preparation of an enantiomericall...

TL;DR: A scalable route capable of producing multikilogram quantities of CI-1034 with no chromatographic steps is described in this contribution, and a remarkably robust Suzuki coupling between a boronic acid and an aromatic sulfonate ester as the key synthetic step is described.

TL;DR: In this article, the effects of various reaction parameters such as reaction temperature, catalyst and substrate concentration, gaseous environment, and acetone concentration on conversion and enantioselectivity were investigated.

TL;DR: In this paper, a scale-up of a new process for the production of 2-chloro-5-trifluoromethyl-benzonitrile by a Sandmeyer reaction was described.

TL;DR: In this article, a statistical analysis of different reactions in terms of kinetics and phases (solid−liquid−gas) is presented to identify sensitive reactions so that a better allocation of resources can be performed from the start of a project.

TL;DR: In this paper, the authors demonstrate the successful synthesis of an array of 1,2-azoles within a borosilicate glass microreactor whereby conversions in the range of 98−100% were obtained.

TL;DR: In this article, a new manufacturing process for clofarabine is presented, which allows for the reliable and efficient production of drug substance in high anomeric excess and high overall purity, without using chromatography.

TL;DR: In this article, an efficient four-step sequence was developed for the synthesis of quinolinone d-tartrate 2 starting from readily available outsourced intermediate 5 in 26% overall yield, including a classical resolution.