Title:
METHODS FOR MAKING 3-O-PROTECTED MORPHINONES AND 3-O-PROTECTED MORPHINONE DIENOL CARBOXYLATES
Document Type and Number:
WIPO Patent Application WO2005077957
Kind Code:
A3
Abstract:
Disclosed are methods for making aldehydes and ketones comprising allowing the corresponding primary or secondary alcohol to react in the presence of trichoroisocyanuric acid, a compound of formula R1SR2 and a base. In one embodiment, the alcohol is a compound of formula (I) wherein R3 is a protecting group. Also disclosed are methods for making 3-O-protected morphine dienol carboxylates comprising allowing a compound of formula (I) to oxidize in the presence of a chlorine-containing compound and a compound of formula R1SR2; and allowing the product of the oxidation step to react with an acylating agent.
Inventors:
STUMPF ANDREAS (US)
Application Number:
PCT/US2005/003390
Publication Date:
May 04, 2006
Filing Date:
February 04, 2005
Export Citation:
Assignee:
EURO CELTIQUE SA (LU)
STUMPF ANDREAS (US)
STUMPF ANDREAS (US)
International Classes:
C07D489/02; C07F7/18; (IPC1-7): C07D489/02
Foreign References:
| US6013796A | 2000-01-11 | |||
| US6177567B1 | 2001-01-23 |
Other References:
COREY ET AL.: "New and highly effective method for the oxidation of primary and secondary alcohols to carbonyl compounds", J. AMER. CHEM. SOC., vol. 94, no. 21, 1972, pages 7586 - 7587, XP002333837
XIONG, ZHI-XING; HUANG, NAN-PING; ZHONG, PING: "A selective and convenient oxidation of sulfides to sulfoxides with trichloroisocyanuric acid", SYNTH. COMMUN., vol. 31, no. 2, 2001, pages 245 - 248, XP009050855
ULF TILSTAM, HILMAR WEINMANN: "TRICHLOROISOCYANURIC ACID: A SAFE AND EFFICIENT OXIDANT", ORGANIC PROCESS RESEARCH & DEVELOPMENT, vol. 6, no. 4, 2002, pages 384-393, XP002334135
SHIN-ICHI OHSUGI, KIYOHARU NISHIDE, KEIJI OONO, KAZUNORI OKUYAMA, MASATO FUDESAKA, SUMIAKI KODAMA AND MANABU NODE: "New odorless method for the Corey?Kim and Swern oxidations utilizing dodecyl methyl sulfide (Dod-S-Me)", TETRAHEDRON, vol. 59, 2003, pages 8393-8398, XP002334136
XIONG, ZHI-XING; HUANG, NAN-PING; ZHONG, PING: "A selective and convenient oxidation of sulfides to sulfoxides with trichloroisocyanuric acid", SYNTH. COMMUN., vol. 31, no. 2, 2001, pages 245 - 248, XP009050855
ULF TILSTAM, HILMAR WEINMANN: "TRICHLOROISOCYANURIC ACID: A SAFE AND EFFICIENT OXIDANT", ORGANIC PROCESS RESEARCH & DEVELOPMENT, vol. 6, no. 4, 2002, pages 384-393, XP002334135
SHIN-ICHI OHSUGI, KIYOHARU NISHIDE, KEIJI OONO, KAZUNORI OKUYAMA, MASATO FUDESAKA, SUMIAKI KODAMA AND MANABU NODE: "New odorless method for the Corey?Kim and Swern oxidations utilizing dodecyl methyl sulfide (Dod-S-Me)", TETRAHEDRON, vol. 59, 2003, pages 8393-8398, XP002334136
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