Chemical Intermediate

a technology of intermediates and oxabispidines, applied in the field of intermediates, can solve the problems of few known processes specifically adapted to the preparation of oxabispidine compounds

Inactive Publication Date: 2009-03-05
ASTRAZENECA AB
View PDF2 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0025]Further, the process of the invention may have the advantage that compounds of formula I may be prepared in higher yields, by way of fewer steps, in less time, more conveniently, and at a lower cost, than when prepared according to the process described in international patent application WO 01 / 28992.

Problems solved by technology

As a result, there are very few known processes that are specifically adapted for the preparation of oxabispidine compounds.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Chemical Intermediate
  • Chemical Intermediate
  • Chemical Intermediate

Examples

Experimental program
Comparison scheme
Effect test

example 1

a) [2-(9-Oxa-3,7-diazabicyclo[3.3.1]non-3-yl)-ethyl]-carbamic acid tert-butyl ester 2,4,6-trimethylbenzenesulfonic acid salt

[0031][2-(7-Benzyl-9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl)-ethyl]-carbamic acid tert-butyl ester 2,4,6-trimethylbenzenesulfonic acid salt (150 g prepared as described below), 4-methyl-2-pentanol (MIBC) (300 mL) and methanol (300 mL) were combined in a metal hydrogenation vessel. Solid 5% Pd / C catalyst (4.5 g, 61% water wet, Johnson Matthey type 440L) was added. The mixture was then hydrogenated under 2.5 bar of hydrogen pressure and was simultaneously heated to 55° C. Gas uptake measurement showed the reaction to be complete after 2 hours. After cooling to 40° C. the catalyst was removed by filtration through a glass fibre filter paper. The catalyst was washed on the filter with MIBC (300 mL) and the washings added to the main filtrate. Solvent (185 mL) was removed by distillation at atmospheric pressure. More solvent (243 mL) was then removed by reduced pressur...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

PropertyMeasurementUnit
temperatureaaaaaaaaaa
temperatureaaaaaaaaaa
13C frequenciesaaaaaaaaaa
Login to View More

Abstract

An acid addition salt of a compound of Formula I, wherein R2 represents C1-6 alkyl (optionally substituted and / or terminated by one or more substituents selected from —OH, halo, cyano, nitro and aryl) or aryl, wherein each aryl and aryloxy group, unless otherwise specified, is optionally substituted.

Description

FIELD OF THE INVENTION[0001]This invention relates to novel intermediates and their use in a process for the preparation of oxabispidine compounds.BACKGROUND TO THE INVENTION[0002]The number of documented compounds including the 9-oxa-3,7-diazabicyclo-[3.3.1]nonane (oxabispidine) structure is very few. As a result, there are very few known processes that are specifically adapted for the preparation of oxabispidine compounds.[0003]Certain oxabispidine compounds are disclosed in Chem. Ber. 96(11), 2827 (1963) as intermediates in the synthesis of 1,3-diaza-6-oxa-adamantanes.[0004]Hemiacetals (and related compounds) having the oxabispidine ring structure are disclosed in J. Org. Chem. 31, 277 (1966), ibid. 61(25), 8897 (1996), ibid. 63(5), 1566 (1998) and ibid. 64(3), 960 (1999) as unexpected products from the oxidation of 1,5-diazacyclooctane-1,3-diols or the reduction of 1,5-diazacyclooctane-1,3-diones.[0005]1,3-Dimethyl-3,7-ditosyl-9-oxa-3,7-diazabicyclo[3.3.1]nonane is disclosed in ...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & AuthorityApplications(United States)
IPC IPC(8): C07D498/08
CPCC07D498/08
InventorCLADINGBOEL, DAVID
OwnerASTRAZENECA AB