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Wednesday 6 January 2016

Hydrocodone






1H-NMR & 13C-NMR of hydrocodone (1)


 hydrocodone as a pale-yellow solid. 
1H NMR (300 MHz, CDCl3) δ 6.72 (d, J = 8.2 Hz, 1H), 6.65 (d, J = 8.2 Hz, 1H), 4.68 (s, 1H), 3.92 (s, 3H), 3.20 (m, 1H), 3.04 (d, J = 18.5 Hz, 1H), 2.59 (m, 2H), 2.49–2.27 (m, 6H), 2.21 (td, J = 11.9, 3.3 Hz, 1H), 2.08 (td, J = 12.0, 4.5 Hz, 1H), 1.86–1.79 (m, 2H), 1.35–1.19 (m, 1H). 

13C NMR (75 MHz, CDCl3) δ 207.89, 145.39, 142.82, 127.24, 126.28, 119.76, 114.47, 91.39, 59.19, 56.75, 56.71, 46.89, 46.83, 42.88, 42.70, 40.23, 35.52, 25.57, 19.95.


HYDROCODONE





Abstract Image
Hydrocodone, a high value active pharmaceutical ingredient (API), is usually produced in a semisynthetic pathway from morphine, codeine or thebaine. The latter alkaloid is an attractive precursor as it is not used as a remedy itself. The key step in this production route is a selective olefin reduction forming 8,14-dihydrothebaine which can be subsequently hydrolyzed to yield hydrocodone. Unfortunately, standard hydrogenation procedures cannot be applied due to severe selectivity problems. A transfer hydrogenation using in situ generated diimide is the only known alternative to achieve a selective transformation. The most (atom) economic generation of this highly unstable reducing agent is by oxidizing hydrazine hydrate (N2H4·H2O) with O2. In the past, this route was “forbidden” on an industrial scale due to its enormous explosion potential in batch. A continuous high-temperature/high-pressure methodology allows an efficient, safe, and scalable processing of the hazardous reaction mixture. The industrially relevant reduction was achieved by using four consecutive liquid feeds (of N2H4·H2O) and residence time units, resulting in a highly selective reduction within less than 1 h.
http://pubs.acs.org/doi/abs/10.1021/acs.oprd.5b00370

Selective Olefin Reduction in Thebaine Using Hydrazine Hydrate and O2under Intensified Continuous Flow Conditions

 Institute of Chemistry, University of Graz, Heinrichstrasse 28, A-8010 Graz, Austria
 Noramco, Inc., 503 Carr Road, Suite 200, Wilmington, Delaware 19809, United States
Org. Process Res. Dev., Article ASAP
DOI: 10.1021/acs.oprd.5b00370
Publication Date (Web): December 15, 2015
Copyright © 2015 American Chemical Society
*E-mail: oliver.kappe@uni-graz.at.



Hydrocodone
Hydrocodone skeletal.svg
Hydrocodone-Spartan-PM3-3D-balls.png
Systematic (IUPAC) name
4,5α-epoxy-3-methoxy-17-methylmorphinan-6-one
Clinical data
Trade namesZohydro ER
AHFS/Drugs.comMicromedex Detailed Consumer Information
MedlinePlusa601006
Pregnancy
category
  • US: C (Risk not ruled out)
    Legal status
    Dependence
    liability
    severe / high
    Routes of
    administration
    oral, intranasal, rectal
    Pharmacokinetic data
    BioavailabilityHigh
    MetabolismHepatic: CYP2D6 (minor; converts tohydromorphone), CYP3A4(major; converts tonorhydrocodone)
    Biological half-life3.8–6 hours
    ExcretionRenal
    Identifiers
    CAS Number125-29-1 Yes
    ATC codeR05DA03
    PubChemCID: 5284569
    IUPHAR/BPS7081
    DrugBankDB00956 Yes
    ChemSpider4447623 Yes
    UNII6YKS4Y3WQ7 Yes
    KEGGD08045 Yes
    ChEBICHEBI:5779 Yes
    ChEMBLCHEMBL1457 Yes
    Synonymsdihydrocodeinone
    Chemical data
    FormulaC18H21NO3
    Molecular mass299.368 g/mol

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