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36282-47-0Relevant articles and documents
Continuous-Flow Synthesis of Tramadol from Cyclohexanone
Monos, Timothy M.,Jaworski, Jonathan N.,Stephens, John C.,Jamison, Timothy F.
, p. 1888 - 1893 (2020/11/24)
A multioperation, continuous-flow platform for the synthesis of tramadol, ranging from gram to decagram quantities, is described. The platform is segmented into two halves allowing for a single operator to modulate between preparation of the intermediate by Mannich addition or complete the fully concatenated synthesis. All purification operations are incorporated in-line for the Mannich reaction. 'Flash' reactivity between meta-methoxyphenyl magnesium bromide and the Mannich product was controlled with a static helical mixer and tested with a combination of flow and batch-based and factorial evaluations. These efforts culminated in a rapid production rate of tramadol (13.7 g°h -1) sustained over 56 reactor volumes. A comparison of process metrics including E-Factor, production rate, and space-time yield are used to contextualize the developed platform with respect to established engineering and synthetic methods for making tramadol.
Catalytic Intramolecular Coupling of Ketoalkenes by Allylic C(sp3)?H Bond Cleavage: Synthesis of Five- and Six-Membered Carbocyclic Compounds
Mita, Tsuyoshi,Sato, Yoshihiro,Uchiyama, Masashi
, (2020/02/05)
In the presence of a catalytic amount of cobalt(II) acetylacetonate/Xantphos in combination with trimethylaluminum, various ketoalkenes underwent an intramolecular cyclization reaction triggered by cleavage of the allylic C(sp3)?H bond, affording carbocyclic compounds with high regio- and diastereoselectivity. Mono-, bi-, and tricarbocyclic compounds were produced in good yields. One of the products thus obtained was derivatized into tramadol in four simple steps. Notably, these intramolecular cyclizations took place in the absence of a gem-disubstituent on the tethered carbon chain (without the Thorpe-Ingold effect). (Figure presented.).
Across-the-World Automated Optimization and Continuous-Flow Synthesis of Pharmaceutical Agents Operating Through a Cloud-Based Server
Fitzpatrick, Daniel E.,Maujean, Timothé,Evans, Amanda C.,Ley, Steven V.
supporting information, p. 15128 - 15132 (2018/10/31)
The power of the Cloud has been harnessed for pharmaceutical compound production with remote servers based in Tokyo, Japan being left to autonomously find optimal synthesis conditions for three active pharmaceutical ingredients (APIs) in laboratories in Cambridge, UK. A researcher located in Los Angeles, USA controlled the entire process via an internet connection. The constituent synthetic steps for Tramadol, Lidocaine, and Bupropion were thus optimized with minimal intervention from operators within hours, yielding conditions satisfying customizable evaluation functions for all examples.
Biomimetic synthesis of Tramadol
Lecerf-Schmidt, Florine,Haudecoeur, Romain,Peres, Basile,Ferreira Queiroz, Marcos Mar?al,Marcourt, Laurence,Challal, Soura,Ferreira Queiroz, Emerson,Sotoing Taiwe, Germain,Lomberget, Thierry,Le Borgne, Marc,Wolfender, Jean-Luc,De Waard, Michel,Robins, Richard J.,Boumendjel, Ahcène
supporting information, p. 14451 - 14453 (2015/09/28)
Tramadol has recently been isolated from the roots and bark of Nauclea latifolia. A plausible biosynthetic pathway has been proposed and the product-precursor relationship has been probed by 13C position-specific isotope analysis. By further exploring this pathway, we demonstrate that a key step of the proposed pathway can be achieved using mild conditions that mimic in vivo catalysis.
COMPOSITIONS AND METHODS FOR OVERCOMING RESISTANCE TO TRAMADOL
-
Paragraph 0210, (2013/03/26)
There is disclosed a composition for oral administration of O-desmethyltramadol. There is further disclosed a method for treating disorders modulated by at least opiate receptor activity or monoamine activity, including acute and chronic pain, comprising administering a pharmaceutical formulation comprising O-desmethyltramadol. Compositions and methods are also provided that are effective for overcoming resistance to tramadol in patients.
Comparative performance evaluation and systematic screening of solvents in a range of Grignard reactions
Kadam, Asha,Nguyen, Mylinh,Kopach, Michael,Richardson, Paul,Gallou, Fabrice,Wan, Zhao-Kui,Zhang, Wei
, p. 1880 - 1888 (2013/09/24)
The solvent effect on the Grignard reaction of benzyl, aryl and heteroaromatic substrates has been systematically evaluated based on reaction efficiency, ease of subsequent work-up, safety and greenness. 2-Methyltetrahydrofuran (2-MeTHF), which can be derived from renewable resources, had at least an equal if not a superior overall process most notably in suppressing the Wurtz coupling by-product from the benzyl Grignard reactions. It is therefore a recommended alternative solvent to Et2O and THF for the preparation of most Grignard reagents and their subsequent reactions.
Reaction of Grignard reagents with carbonyl compounds under continuous flow conditions
Riva,Gagliardi,Martinelli,Passarella,Vigo,Rencurosi
experimental part, p. 3242 - 3247 (2010/05/19)
This contribution details how a continuous flow reactor was used to react carbonyl compounds with Grignard reagents at room temperature in an efficient and safe manner. Flow rate, residence time and temperature were optimized for the preparation of a small collection of secondary and tertiary alcohols. Excellent yields and general applicability were observed using the set-up protocol. The procedure was also applied for the preparation of Tramadol, an analgesic drug belonging to the opioid group. The developed conditions allowed the selective addition of Grignard reagents to aldehydes and ketones in the presence of a nitrile function.
METHOD FOR THE PRODUCTION OF 2-[(DIMETHYLAMINO)METHYL]-1-(3-METHOXYPHENYL)CYCLOHEXANOL
-
Page/Page column 6-7; 8, (2010/02/06)
The invention relates to a method for the production of 2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexanol with high stereoselectivity and in high yield.
Application of microreactor technology in process development
Zhang, Xini,Stefanick, Stephen,Villani, Frank J.
, p. 455 - 460 (2013/09/05)
The microreactor 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. Applications to several classes of reactions including highly exothermic reactions, high-temperature reactions, reactions with unstable intermediates, and reactions involving hazardous reagents are described herein.
Development of highly efficient resolutions of racemic tramadol using mandelic acid
Evans, Graham R.,Fernandez, Paloma Diaz,Henshilwood, James A.,Lloyd, Steve,Nicklin, Chris
, p. 729 - 737 (2013/09/06)
Two methods for the resolution of tramadol are described. One uses the active pharmaceutical ingredient (API), tramadol hydrochloride as input material. The other utilises the crude free base obtained from the Grignard reaction on tramadol Mannich base. B