WO2006105357A3 - Electrochemical method for the production of betulin aldehyde - Google Patents

Electrochemical method for the production of betulin aldehyde Download PDF

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Publication number
WO2006105357A3
WO2006105357A3 PCT/US2006/011794 US2006011794W WO2006105357A3 WO 2006105357 A3 WO2006105357 A3 WO 2006105357A3 US 2006011794 W US2006011794 W US 2006011794W WO 2006105357 A3 WO2006105357 A3 WO 2006105357A3
Authority
WO
WIPO (PCT)
Prior art keywords
betulin
aldehyde
production
betulinic acid
electrochemical method
Prior art date
Application number
PCT/US2006/011794
Other languages
French (fr)
Other versions
WO2006105357A2 (en
Inventor
Pavel A Krasutsky
Andriy B Khotkevych
Alexei Pushechnikov
Anna Rudnitskaya
Original Assignee
Univ Minnesota
Pavel A Krasutsky
Andriy B Khotkevych
Alexei Pushechnikov
Anna Rudnitskaya
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Univ Minnesota, Pavel A Krasutsky, Andriy B Khotkevych, Alexei Pushechnikov, Anna Rudnitskaya filed Critical Univ Minnesota
Priority to US11/910,134 priority Critical patent/US20080308426A1/en
Publication of WO2006105357A2 publication Critical patent/WO2006105357A2/en
Publication of WO2006105357A3 publication Critical patent/WO2006105357A3/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
    • C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
    • C25B3/00—Electrolytic production of organic compounds
    • C25B3/20—Processes
    • C25B3/23—Oxidation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Electrochemistry (AREA)
  • Materials Engineering (AREA)
  • Metallurgy (AREA)
  • Steroid Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The present invention provides a method for manufacturing betulin aldehyde from betulin. The method includes: (a) electrochemically forming a oxoammonium ion from a nitroxyl radical; and (b) contacting betulin with the oxoammonium ion, for a period of time effective to provide the betulin aldehyde. The betulin aldehyde can subsequently be converted to betulinic acid, employing, e.g., NaClO2 or KClO2. The betulinic acid can be purified from from any unreacted betulin by converting the betulinic acid into a corresponding salt (Na, K, Li, Na, Ca, Mg, Ba, or Al), and separating the salt from the unreacted betulin.
PCT/US2006/011794 2005-03-29 2006-03-29 Electrochemical method for the production of betulin aldehyde WO2006105357A2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US11/910,134 US20080308426A1 (en) 2005-03-29 2006-03-29 Electrochemical Method for the Production of Betulin Aldehyde

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US66602005P 2005-03-29 2005-03-29
US60/666,020 2005-03-29

Publications (2)

Publication Number Publication Date
WO2006105357A2 WO2006105357A2 (en) 2006-10-05
WO2006105357A3 true WO2006105357A3 (en) 2007-06-14

Family

ID=37054156

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2006/011794 WO2006105357A2 (en) 2005-03-29 2006-03-29 Electrochemical method for the production of betulin aldehyde

Country Status (2)

Country Link
US (1) US20080308426A1 (en)
WO (1) WO2006105357A2 (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9217000B2 (en) 2011-02-18 2015-12-22 Univerisyt of Pittsburgh—of the Commonwealth System of Higher Education Targeted nitroxide agents
SE1150819A1 (en) * 2011-09-12 2013-03-13 Stora Enso Oyj Procedure for derivatization of a chemical component in wood

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH02107790A (en) * 1988-10-14 1990-04-19 Osaka Organic Chem Ind Ltd Oxidation of primary alcohol to aldehyde with high selectivity
US6232481B1 (en) * 2000-01-11 2001-05-15 Regents Of The University Of Minnesota Method for manufacturing betulinic acid
WO2006063464A1 (en) * 2004-12-15 2006-06-22 Universite De Sherbrooke Process for preparing betulinic acid

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5344563A (en) * 1976-10-05 1978-04-21 Ouchi Shinkou Kagaku Kougiyou Preparation of benzothiazolylsulfenamide

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH02107790A (en) * 1988-10-14 1990-04-19 Osaka Organic Chem Ind Ltd Oxidation of primary alcohol to aldehyde with high selectivity
US6232481B1 (en) * 2000-01-11 2001-05-15 Regents Of The University Of Minnesota Method for manufacturing betulinic acid
WO2006063464A1 (en) * 2004-12-15 2006-06-22 Universite De Sherbrooke Process for preparing betulinic acid

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
SEMMELHACK M F ET AL: "Nitroxyl -mediated electrooxidation of alcohols to aldehydes and ketones", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC, US, vol. 105, no. 13, 1983, pages 4492 - 4494, XP002385263, ISSN: 0002-7863 *
SÜMMERMANN W, DEFFNER U: "Die elektrochemische Oxidation aliphatischer Nitroxyl-Radikale", TETRAHEDRON, vol. 31, no. 6, 1975, pages 593 - 596, XP002427937 *

Also Published As

Publication number Publication date
US20080308426A1 (en) 2008-12-18
WO2006105357A2 (en) 2006-10-05

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