2-Carbomethoxytropinone

2-Carbomethoxytropinone Carbomethoxytropinone.svg skin-invert-image 200px Methyl 3-oxotropane-2β-carboxylate Methyl (1R,2R,5S)-8-methyl-3-oxo-8-azabicyclo[3.2.1]octane-2-carboxylate Carbomethoxy-tropinone; 2-Carbomethoxy-3-tropinone; Carbmethoxy-tropinone; Methyl 8-methyl-3-oxobicyclo[3.2.1]octane-2-carboxylate; Methyl 8-methyl-3-oxo-8-azabicyclo[3.2.1]octane-4-carboxylate; 2-(Methoxycarbonyl)-3-tropanone CAS 36127-17-0 67115 changed chemspider 220720 1S/C10H15NO3/c1-11-6-3-4-7(11)9(8(12)5-6)10(13)14-2/h6-7,9H,3-5H2, 1-2H3/t6-,7+,9+/m0/s1 WXEMSGQRTGSYOG-LKEWCRSYSA-N 11127215 CN1[C@H]2CC[C@@H]1[C@H](C(=O)C2)C(=O)OC 10 15 1 3 104 2-Carbomethoxytropinone (2-CMT) is a commonly used organic intermediate in the synthesis of cocaine and its analogues.10.1021/jo01362a022 Concerning 2-Carbomethoxytropinone* 1957 Findlay Stephen P. The Journal of Organic Chemistry 22 11 1385–1394 As of at least 1999 no reaction pathway has been discovered that synthesizes cocaine-like compounds without utilizing the reduction of 2-CMT.10.1016/S0014-827X(99)00027-0 Two-carbon bridge substituted cocaines: Enantioselective synthesis, attribution of the absolute configuration and biological activity of novel 6- and 7-methoxylated cocaines 1999 Simoni Daniele Roberti Marinella Andrisano Vincenza Manferdini Monica Rondanin Riccardo Invidiata Francesco Paolo Il Farmaco 54 5 275–87 10418122 The structure of cocaine was discovered by Richard Willstätter in 1898 after he synthesized it from 2-carbomethoxytropinone.10.1039/b001713m Tropane alkaloid biosynthesis. A century old problem unresolved 2001 Humphrey Andrew J. O'Hagan David Natural Product Reports 18 5 494–502 1169988210.1021/ja01640a001 The Three-dimensional Structure of the Cocaines. Part I. Cocaine and Pseudococaine 1954 Findlay Stephen P. Journal of the American Chemical Society 76 11 2855–2862 1954JAChS..76.2855F Although it was originally believed that 2-CMT in nature was ultimately derived from ornithine and acetic acid,10.1021/ja00360a038 Chemistry of the tropane alkaloids. 33. 2-Carbomethoxy-3-tropinone: An advanced intermediate in the biosynthesis of cocaine 1983 Leete Edward Journal of the American Chemical Society 105 22 6727–6728 1983JAChS.105.6727L subsequent research has indicated other pathways exist for the biosynthesis of 2-CMT.10.1021/ja00217a051 A revision of the generally accepted hypothesis for the biosynthesis of the tropane moiety of cocaine 1988 Leete Edward. Kim Sung Hoon. Journal of the American Chemical Society 110 9 2976 1988JAChS.110.2976L 10.1016/B978-0-12-408061-4.00002-X Increasing the Pace of New Discoveries in Tropane Alkaloid Biosynthesis New Light on Alkaloid Biosynthesis and Future Prospects Advances in Botanical Research 2013 Jirschitzka Jan Dolke Franziska d’Auria John C. 9780124080614 68 39 A β-keto ester, 2-CMT exists in equilibrium with its keto–enol tautomer. Synthesis 2-CMT (3) can be synthesized from 1,3-acetonedicarboxylate anhydride (1) by methanolysis followed by reaction with methylamine and succinaldehyde.Proc F. according to FindlayAugust 2016 class=skin-invert-image|left|700px|thumb|Synthesis of 2-CMT See also Tropinone References Category:Tropanes Category:Ketones Category:Methyl esters