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1. (WO2001032617) PROCESS FOR THE PREPARATION OF 7-AZABICYCLO[4.1.0]-HEPT-3-ENE-3-CARBOXYLIC ACID ESTERS
Latest bibliographic data on file with the International Bureau   

Pub. No.:    WO/2001/032617    International Application No.:    PCT/JP2000/007578
Publication Date: 10.05.2001 International Filing Date: 27.10.2000
Chapter 2 Demand Filed:    28.03.2001    
IPC:
C07C 227/08 (2006.01), C07C 229/48 (2006.01), C07C 229/64 (2006.01), C07D 203/02 (2006.01), C07D 203/26 (2006.01)
Applicants: SAGAMI CHEMICAL RESEARCH CENTER [JP/JP]; 4-1, Nishiohnuma 4-chome, Sagamihara-shi, Kanagawa 229-0012 (JP) (For All Designated States Except US).
KURARAY CO., LTD. [JP/JP]; 1621, Sakazu, Kurashiki-shi, Okayama 710-8622 (JP) (For All Designated States Except US).
TERASHIMA, Shiro [JP/JP]; (JP) (For US Only).
UJITA, Katsuji [JP/JP]; (JP) (For US Only).
ISHIWATA, Akihiro [JP/US]; (US) (For US Only)
Inventors: TERASHIMA, Shiro; (JP).
UJITA, Katsuji; (JP).
ISHIWATA, Akihiro; (US)
Agent: TAKASHIMA, Hajime; Fujimura Yamato Seimei Building, 2-14, Fushimimachi 4-chome, Chuo-ku, Osaka-shi, Osaka 541-0044 (JP)
Priority Data:
11/312616 02.11.1999 JP
Title (EN) PROCESS FOR THE PREPARATION OF 7-AZABICYCLO[4.1.0]-HEPT-3-ENE-3-CARBOXYLIC ACID ESTERS
(FR) ELABORATION D'ESTERS D'ACIDE 7-AZABICYCLO[4.1.0]-HEPT-3-ENE-3-CARBOXYLIQUE
Abstract: front page image
(EN)A process for preparing 7-azabicyclo[4.1.0]hept-3-ene-3-carboxylic acid esters (VII) inexpensively, industrially advantageously, efficiently and on a large scale. This process is characterized by comprising reacting an epoxide (I) with an amine (II) to obtain an aminodiol (III), reacting this aminodiol (III) with a sulfonylating agent in the presence of a base to obtain an azabicyclohept-2-ene (IV), reacting the obtained compound (IV) with an alcohol (V) in the presence of a Lewis acid to obtain an azabicyclohept-3-ene (VI), and eliminating the 7-position substituent, R2, from the azabicyclohept-3-ene (VI).
(FR)La présente invention concerne un procédé puissant et peu coûteux de production industrielle de grandes quantités d'esters d'acide 7-azabicyclo[4.1.0]-hept-3-ène-3-carboxylique (VII). A cet effet, on fait réagir avec un amine (II) un époxyde (I), ce qui donne un aminodiol (III). On fait alors réagir avec un agent de sulfonylation cet aminodiol (III) en présence d'une base de façon à obtenir un azabicyclohept-2-ène. On fait ensuite réagir avec un alcool (V) en présence d'un acide de Lewis le composé obtenu (IV), ce qui donne un azabicyclohept-3-ène (VI). Il ne reste plus qu'à éliminer le substituant R2 en position 7 de l'azabicyclohept-3-ène (VI).
Designated States: AU, CA, CN, IN, US.
European Patent Office (AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IT, LU, MC, NL, PT, SE).
Publication Language: Japanese (JA)
Filing Language: Japanese (JA)