60723-43-5

Usage

Uses

Used in Pharmaceutical Industry:
9-Acetoxyrubanone is used as an intermediate for the synthesis of (3S)-3-Hydroxy Quinidine, which is a compound with potential applications in the development of new drugs and therapies. Its role as an intermediate is crucial in the chemical synthesis process, allowing for the creation of the desired end product with specific properties and functions.

InChI:InChI=1/C20H22N2O4/c1-12(23)26-20(18-9-13-6-8-22(18)11-19(13)24)15-5-7-21-17-4-3-14(25-2)10-16(15)17/h3-5,7,10,13,18,20H,6,8-9,11H2,1-2H3/t13?,18-,20+/m1/s1

Upstream product

• 56-54-2 (+)-quinidine 
• 53922-99-9 α-10-bromodihydroquinidine 
• 139237-97-1 (S)-((2R)-5-ethylidene-1-azabicyclo[2.2.2]oct-2-yl)-(6-methoxy-quinoline-4-yl)-methanol 
• 139239-49-9 apoquinidine methyl ether 9-acetate 

Downstream Products

• 60761-51-5 (3R)-3-hydroxyquinidine 
• 53467-23-5 3-hydroxyquinidine 
• 60723-44-6 (3S)-3-hydroxyquinidine 9-benzoate 

Relevant academic research and scientific papers

A Tricyclic Dehydrorubanone and New Isomers of the Major Quinidine Metabolite

Spiroepoxide 1 was prepared from quinidine and converted into β-amino alcohol 3 (86percent over two steps).Dihydroxylation of enantiopure oxazatricylic olefin (E)-4 provided diastereomeric diols 5a and 5b.Stereospecific conversion of 1,2-secondary, tertiary diol 5b into tetracyclic spiroepoxide 6 was accomplished in high yield by a one-pot tosylation-cyclization procedure. 1,2-Diol cleavage with NaIO4 in 80percent acetic acid afforded the new tricyclic dehydrorubanone 7, containing the 4-oxa-7-azatricyclo3,7>decan-2-one core structure.Similarly, acetylated rubanone 9 was prepared on a 20 g scale.Reduction with NaBH4 in the presence of CeCl3 provided rubanols 10a and 10b (1:1.1).Horner-Wittig reaction of 9 with diethyl cyanomethylphosphonate was (Z)-selective, furnishing unsaturated nitrile (Z)-13.Conversion into the α,β-unsaturated aldehyde (Z)-14 and reduction afforded enantiopure allylic alcohol (Z)-12, which is a new isomer of the key quinidine metabolite 15. - Keywords: amino alcohols; asymmetric ayntheses; dihydroxylations; diol cleavage Horner-Wittig reaction

(3S)-3-Hydroxyquinidine, the Major Biotransformation Product of Quinidine. Synthesis and Conformational Studies. X-Ray Molecular Structure of (3S)-3-Hydroxyquinidine Methanesulphonate

(3S)-3-Hydroxyquinidine, the major metabolite of the Cinchona alkaloid quinidine, was prepared by synthetic chemical modification or microbial oxidation of quinidine.The structure of this metabolite has been demonstrated to be (3S)-3-hydroxyquinidine by 1H and 13C NMR, IR, UV and mass spectral analysis.Previously published comparisons of the 13C NMR spectra of 3-hydroxyquinidine and model compounds were used to establish the absolute stereochemistry of the metabolite (see ref. 8).This assignment has been verified by single-crystal X-ray analysis of (3S)-3-hydroxyquinidine methanesulphonate.The gas- and solution-phase conformational preference of the metabolite derived from molecular modelling and NOE studies are compared with the conformation observed by X-ray crystallography.